Water → HCID 57963186, compound

HRID 1775167Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To {5-[(7-Benzenesulfonyl-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(2-chloro-benzyl)-carbamic acid tert-butyl ester (44, 0.400 g, 0.612 mmol) in 15.0 mL of 1,2-dichloroethane, triethylsilane (2.0 mL, 12 mmol) and trifluoroacetic acid (1.0 mL, 13 mmol) were added. The reaction was heated at 80° C. for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (45, 0.30 g).

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under vacuum
customThe resulting material was purified by silica gel chromatography
washeluting with 20-100% ethyl acetate in hexane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-504909e0d22e406592fcd4862bb69f5f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260437B2

Reaction notes

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