Trifluoroacetic acid → HCID 57619455, compound

HRID 1256774Notes

Reaction equation

[C:1]([O:5][C:6](=[O:42])[N:7]([C:15]1[S:16][C:17]([CH:21](O)[C:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[N:24]([Si](C(C)C)(C(C)C)C(C)C)[CH:23]=2)=[C:18]([Cl:20])[N:19]=1)[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[C:1]([O:5][C:6](=[O:42])[N:7]([C:15]1[S:16][C:17]([CH2:21][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[C:18]([Cl:20])[N:19]=1)[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {4-chloro-5-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-thiazol-2-yl}-pyridin-4-ylmethyl-carbamic acid tert-butyl ester (519, 0.397 g, 0.57 mmol), triethylsilane (1.0 mL, 6.3 mmol), and trifluoroacetic acid (0.5 mL, 6 mmol) in acetonitrile (10 mL) was stirred at 40° C. for 2 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with sodium bicarbonate, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the desired compound as a yellow solid (520, 126 mg, 49%). MS (ESI) [M+H+]+=456.2.

Workup

extractionextracted with ethyl acetate
washwashed with sodium bicarbonate
washwashed with brine
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe residue was purified by silica gel column chromatography
washeluting with methanol in dichloromethane

Sources & evidence

ORD record: ord-b381d1587f2f4f85927c1a3fe23e8b7c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461169B2

Reaction notes

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