Chlorotrimethylsilane → 1-(4-(4-(4-(1H-indazol-6-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

HRID 645672Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[N:27][NH:28]3)=[CH:24][CH:23]=2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][N:41]([C:44](=[O:46])[CH3:45])[CH2:40][CH2:39]2)=[CH:34][CH:33]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:28]1[C:29]2[C:25](=[CH:24][CH:23]=[C:22]([NH:21][C:4]3[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=[C:2]([NH:31][C:32]4[CH:33]=[CH:34][C:35]([N:38]5[CH2:39][CH2:40][N:41]([C:44](=[O:46])[CH3:45])[CH2:42][CH2:43]5)=[CH:36][CH:37]=4)[N:3]=3)[CH:30]=2)[CH:26]=[N:27]1

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of 2-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (340 mg, 0.78 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (204 mg, 0.93 mmol) and trimethylsilyl chloride (TMSCl) (0.200 mL, 1.58 mmol) in n-butyl alcohol (8 mL) was heated at 116° C. overnight. More 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (204 mg, 0.93 mmol) was added. The mixture was then stirred at 116° C. for another 48 h. It was then purified by HPLC to give 1-(4-(4-(4-(1H-indazol-6-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone as a solid (126 mg).

Workup

customIt was then purified by HPLC

Sources & evidence

ORD record: ord-ada1a4eebe8f469f88b88cf940b1c816
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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