Potassium Carbonate → HCID 73602904, compound

HRID 1915884Notes

Reaction equation

HRID 1915884 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH:17][C:18]2[CH:19]=[N:20][N:21]([CH2:37][CH:38]([F:40])[F:39])[C:22]=2[N:23]2[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30]C(=O)C(F)(F)F)[CH2:25][CH2:24]2)=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[C:3]([C:15]([NH:17][C:18]2[CH:19]=[N:20][N:21]([CH2:37][CH:38]([F:40])[F:39])[C:22]=2[N:23]2[CH2:29][CH2:28][CH2:27][C@@H:26]([NH2:30])[CH2:25][CH2:24]2)=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86680088HCID 86680088, compound

Product 1

HCID 73602904HCID 73602904, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-amino-N-(1-(2,2-difluoroethyl)-5-(4-(2,2,2-trifluoroacetamido)azepan-1-yl)-1H-pyrazol-4-yl)-6-(2-fluorophenyl)picolinamide (98 mg, 0.17 mmol) was stirred with potassium carbonate (144 mg, 1.03 mmol) in methanol (5 mL) at 50° C. overnight. The mixture was filtered and the filtrate was purified on reversed phase HPLC to give 180. 1H NMR (400 MHz, DMSO) δ 9.81 (s, 1H), 8.00 (td, J=8.3, 1.8 Hz, 1H), 7.86 (s, 1H), 7.74 (dd, J=8.7, 2.2 Hz, 1H), 7.43 (dt, J=7.2, 3.8 Hz, 1H), 7.38-7.20 (m, 4H), 7.08 (s, 2H), 6.38 (tt, J=55.3, 4.1 Hz, 1H), 4.43 (td, J=14.5, 4.1 Hz, 2H), 3.55 (s, 1H), 3.21-3.07 (m, 4H), 2.92 (dd, J=19.4, 10.4 Hz, 1H), 1.89-1.69 (m, 3H), 1.69-1.37 (m, 3H). MS (ESI) m/z: 474.2 [M+H+].

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified on reversed phase HPLC

Sources & evidence

ORD record
ord-3db4254c058c4f388d4f964cdd6fb56e
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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