Chlorotrimethylsilane → HCID 178473886, compound

HRID 645678Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]3[C:25]([C:26]([CH3:31])=[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.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][N:42]([C:45](=[O:47])[CH3:46])[CH2:41][CH2:40]2)=[CH:35][CH:34]=1.C[Si](Cl)(C)C>CCCCO>[CH3:31][C:26]1[C:25]2[C:29](=[CH:30][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:32][C:33]4[CH:34]=[CH:35][C:36]([N:39]5[CH2:40][CH2:41][N:42]([C:45](=[O:47])[CH3:46])[CH2:43][CH2:44]5)=[CH:37][CH:38]=4)[N:3]=3)=[CH:23][CH:24]=2)[NH:28][N:27]=1

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of 2-chloro-N-(3-methyl-1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (260 mg, 0.574 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (251 mg, 1.15 mmol) and trimethylsilyl chloride (TMSCl) (0.150 mL, 1.19 mmol) in n-BuOH (5 mL) was heated at 116° C. for 48 h. It was then purified by HPLC to give 1-(4-(4-(4-(3-methyl-1H-indazol-6-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (30 mg).

Workup

customIt was then purified by HPLC

Sources & evidence

ORD record: ord-85a2c70cf3e241c9a7e847de72635421
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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