Chlorotrimethylsilane → 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 2381618Notes

Reaction equation

HRID 2381618 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=[O:18])[CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][N:30]([C:33](=[O:35])[CH3:34])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C[Si](Cl)(C)C>CCCCO>[N:27]1([C:24]2[CH:23]=[CH:22][C:21]([NH:20][C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=[O:18])[CH2:13][CH2:12]4)[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)=[CH:26][CH:25]=2)[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]1.[C:33]([N:30]1[CH2:29][CH2:28][N:27]([C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=[O:18])[CH2:13][CH2:12]4)[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)=[CH:22][CH:23]=2)[CH2:32][CH2:31]1)(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 579902901-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Product 2

HCID 444676091-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideHCID 444677451-(2-(4-(piperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 1-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (80 mg, 0.28 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (125 mg, 0.57 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in n-BuOH (3 mL) was stirred at 130° C. for 20 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give 1-(2-(4-(piperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (4 mg) (MS 421.5 (M+H)) and 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (6 mg) (MS 463.5 (M+H); UV 200.0, 272.8 nm).

Workup

  1. customwas removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-a7cfd270cd434423822fffa1ec76d07b
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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