Trifluoroacetic acid → HCID 67041061, compound

HRID 605335Notes

Reaction equation

HRID 605335 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:31])[NH:22][C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])=[CH:17][C:16]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>ClCCl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C@H:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH3:24])=[O:31])=[CH:17][C:16]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67040380HCID 67040380, compound

Product 1

HCID 67041061HCID 67041061, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-{4-[2-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(1-phenyl-ethylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid tert-butyl ester (80 mg) in dichloromethane (1.6 mL) was added trifluoroacetic acid [TFA] (0.40 mL) dropwise at room temperature and the mixture was stirred at room temperature for 1 hour. The reaction mixture was portioned between AcOEt and aqueous K2CO3. The organic layer was separated, washed with H2O and brine, dried over MgSO4, and evaporated to pale yellow amorphous, which was solidified by trituration in i-Pr2O. The resulting solid was collected by filtration, washed with i-Pr2O, and dried at 40° C. overnight under reduced pressure to give the title compound as yellow crystal (57 mg, 85%). 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=7.0 Hz, 6H), 1.45 (d, J=7.3 Hz, 3H), 3.23 (septet, J=7.0 Hz, 1H), 5.15 (quintet, J=7.3 Hz, 1H), 5.58 (s, 2H), 6.62 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.5 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 7.16-7.25 (m, 1H), 7.25-7.40 (m, 4H), 7.63 (d, J=8.4 Hz, 1H), 7.71 (dd, J=8.5, 1.8 Hz, 1H), 7.88 (d, J=1.8 Hz, 1H), 8.57 (s, 1H), 8.75 (d, J=7.3 Hz, 1H), 8.87 (d, J=8.5 Hz, 1H), 10.12 (s, 1H) MS ESI+ m/z: 535 (M+H)

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customevaporated to pale yellow amorphous, which
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with i-Pr2O
  7. customdried at 40° C. overnight under reduced pressure

Sources & evidence

ORD record
ord-ef7e29f17e3d4e589850b44355efc73f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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