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Sally reminded me to ask you to tell Bob to remember to bring his soccer ball to the picnic.

The sentence above, somehow seems unnatural and not good to me. Can I alternate with gerunds as follows?

Sally reminded me to ask you telling Bob to remember bringing his soccer ball to the picnic.

I hope you don't mind to explain if the sentence can't be changed using gerunds.

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    Your first sentence, although a mouthful, is correct. Your second doesn't work at all. In short, you cannot use gerunds in this way. May 11 at 0:02
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  1. Sally reminded me to ask you to tell Bob to remember to bring his soccer ball to the picnic.
  1. Sally reminded me to ask you telling Bob to remember bringing his soccer ball to the picnic.

Example 1 is grammatical.

Example 2 does not convey the same message and its meaning is unclear.

The to-infinitive form and the + ing form give different meanings. The form to tell/ to bring focuses on the intention; telling/ bringing focuses on the effect of something done. In another word, the former is prospective, and the latter is retrospective.

The context of your example requires the verbs to be prospective, and the + ing form is not possible.

Context aside, ask belongs to the following category and cannot be followed by you telling.

Verbs followed by a direct object and a to-infinitive

Some verbs are used with a direct object...followed by a to-infinitive.

Cambridge Dictionary

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