Methanol → HCID 58456285, compound

HRID 410655Notes

Reaction equation

HRID 410655 reaction equation
[OH:1][C@@:2]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:7][CH2:6][C@@H:5]([C:8]([OH:10])=[O:9])[C:4]([CH3:12])([CH3:11])[CH2:3]1.S(=O)(=O)(O)O.[CH3:41]O>O>[OH:1][C@@:2]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:41])=[O:9])[C:4]([CH3:11])([CH3:12])[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 53251507HCID 53251507, compound

Product 1

HCID 58456285HCID 58456285, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1R,4S)-4-hydroxy-2,2-dimethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (100 mg, 0.197 mmol) was dissolved in methanol (3 ml) and concentrated sulfuric acid (10.52 μl, 0.197 mmol) added. The reaction mixture was stirred for 16 hours. The reaction mixture was diluted with water, extracted with ethyl acetate (3×) and washed with saturated aqueous sodium bicarbonate. Solvent evaporation gave the title compound (85 mg, 0.163 mmol, 83% yield). MS ESI: [M+H]+ m/z 521.1. 1H NMR (500 MHz, DMSO-d6) 1H NMR δ 10.25 (s, 1H), 8.83 (d, J=4.9, 1H), 7.93 (s, 2H), 7.46 (s, 1H), 7.28 (d, J=4.9, 1H), 7.14 (s, 1H), 5.92 (s, 1H), 3.59 (s, 3H), 2.31 (s, 4H), 1.84 (s, 3H), 1.65 (m, 3H), 1.08 (s, 3H), 0.96 (s, 3H). rhSYK activity=+++

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customSolvent evaporation

Sources & evidence

ORD record
ord-87728b4c234a490bbb2fe79d9a7dcfac
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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