Trifluoroacetic acid → HCID 58485691, compound

HRID 1396175Notes

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]([CH:33]4[CH2:35][CH2:34]4)=[N:30][CH:29]=[N:28][C:27]=3[N:26]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:25]=2)O)=[C:18]([F:45])[N:17]=1)[C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[C:39]1([S:36]([N:26]2[C:27]3[N:28]=[CH:29][N:30]=[C:31]([CH:33]4[CH2:34][CH2:35]4)[C:32]=3[C:24]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([NH:7][C:8]4[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=4)=[N:17][C:18]=3[F:45])=[CH:25]2)(=[O:38])=[O:37])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To {5-[(7-benzenesulfonyl-4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(6-methoxy-pyridin-3-yl)-carbamic acid tert-butyl ester (75, 0.290 g, 0.448 mmol) in 9.93 mL of 1,2-dichloroethane, triethylsilane (0.31 mL, 2.0 mmol) and trifluoroacetic acid (0.16 mL, 2.0 mmol) are added and the reaction stirred at 80° C. for 4 hours. The reaction is poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried with sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (76, 170 mg). MS (ESI) [M+H+]+=530.9.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer is dried with sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record: ord-376c90894018495aa359fe34337cd2a8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901118B2

Reaction notes

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