HCID 69309475, compound → HCID 69309582, compound

HRID 1947049Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]3[CH2:35][CH2:34][CH:33]([N:36]([CH2:41][CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[S:37]([CH3:40])(=[O:39])=[O:38])[CH2:32][CH2:31]3)[N:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)C(F)(F)F>[C:47]([Si:44]([CH3:46])([CH3:45])[O:43][CH2:42][CH2:41][N:36]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:33]1[CH2:34][CH2:35][CH:30]([NH:29][C:25]2[N:24]=[C:23]([N:18]3[C:19]4[C:15](=[C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:17]3)[CH:28]=[CH:27][N:26]=2)[CH2:31][CH2:32]1)([CH3:48])([CH3:50])[CH3:49]

Participants

Conditions

Temperature: 150 °C

Procedure

4-{1-[2-(4-{[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclo-hexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-piperazin-1-carboxylic acid t-butyl ester (0.251 g, 0.345 mmol) and hexafluoroisopropanol (10 mL) were combined and heated to 150° C. for 2 h in a microwave oven. The solvent was removed in vacuo to yield crude 1-{1-[2-(4-{[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclohexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-piperazine (0.267 g). This intermediate (0.193 g) and acetic anhydride (0.03 mL) in NMP (0.3 mL) was allowed to stir at RT for 6 h. EtOAc and water were then added, the organic layer separated and the organic layers combined, washed with water, sat. NaHCO3, dried over sodium sulfate, filtered, the solvent removed in vacuo, and the product purified on a silica column eluting with 0% to 10% MeOH/EtOAc to yield 1-{1-[2-(4-{[2-(t-butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclohexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-4-acetyl-piperazine (0.119 g, 58%).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-8bbfd038cbd448d1b9576cb4febe0ed3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

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