Trifluoroacetic acid → HCID 11606207, compound

HRID 221901Notes

Reaction equation

HRID 221901 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:42][CH2:43][O:44][Si](C)(C)C(C)(C)C)[C:10]1[CH:11]=[C:12]([N:16]2[C:20]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[O:23])=[CH:19][C:18]([C:38]([CH3:41])([CH3:40])[CH3:39])=[N:17]2)[CH:13]=[CH:14][CH:15]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>CO.O.C(Cl)Cl>[OH:6][CH2:7][CH2:8][N:9]([CH2:42][CH2:43][OH:44])[C:10]1[CH:11]=[C:12]([N:16]2[C:20]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=4)=[CH:27][CH:26]=3)=[O:23])=[CH:19][C:18]([C:38]([CH3:39])([CH3:40])[CH3:41])=[N:17]2)[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53630196HCID 53630196, compound

Product 1

HCID 11606207HCID 11606207, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(3-{bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-phenyl)-5-tert-butyl-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)-phenyl]-urea (153 mg, 0.20 mmol) in methanol (2 mL) was added a solution of 10% TFA in H2O (2 mL). The reaction was stirred at room temperature for 4 h. The mixture was then diluted with DCM, basified by addition of saturated NaHCO3 and extracted with DCM. The combined organic phases were washed with brine, dried over MgSO4, and concentrated at reduced pressure. The residue was purified by MPLC (eluting with 3% to 6% MeOH in DCM) to give 35 mg (36%) of the desired product. 1H-NMR (DMSO-d6) δ 9.17 (s, 1H), 8.40 (dd, J=1.5 & 4.7 Hz, 2H), 8.32 (s, 1H), 7.48 (d, J=8.8 Hz, 2H), 7.26-7.22 (m, 1H), 7.07 (d, J=9.1 Hz, 2H), 6.85 (dd, J=1.5 & 4.7 Hz, 2H), 6.71-6.69 (m, 2H), 6.63 (d, J=7.9 Hz, 1H), 6.34 (s, 1H), 4.76 (t, J=5.4 Hz, 2H), 3.54 (q, J=5.7 Hz, 4H), 3.43 (t, J=5.7 Hz, 4H), 1.26 (s, 9H); MS LC-MS [M+H]+=531.2, RT=2.27 min.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by MPLC (eluting with 3% to 6% MeOH in DCM)

Sources & evidence

ORD record
ord-1fa7f606462e40fda7ac298ad3d1d73c
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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