Trifluoroacetic acid → HCID 58485832, compound

HRID 1396178Notes

Reaction equation

HRID 1396178 reaction equation
C(OC(=O)[N:7]([C:16]1[CH:21]=[CH:20][C:19]([C: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:23])=[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.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]([C:22]([C:19]3[C:18]([F:45])=[N:17][C:16]([NH:7][C:8]4[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=4)=[CH:21][CH:20]=3)=[O:23])=[CH:25]2)(=[O:38])=[O:37])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58485787HCID 58485787, compound

Product 1

HCID 58485832HCID 58485832, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To [5-(7-benzenesulfonyl-4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-6-fluoro-pyridin-2-yl]-(6-methoxy-pyridin-3-yl)-carbamic acid tert-butyl ester (77, 0.340 g, 0.527 mmol) in 10 mL of 1,2-dichloroethane, trifluoroacetic acid (0.80 mL, 10.4 mmol) is added. The reaction is stirred at 80° C. for 45 minutes, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (78, 235 mg). MS (ESI) [M+H+]+=545.4.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-748d870268a84899b3280ad8fbf74287
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

Loading…