Ethanol → HCID 58456256, compound

HRID 410654Notes

Reaction equation

HRID 410654 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.[CH2:41](O)[CH3:42]>>[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][CH2:41][CH3:42])=[O:9])[C:4]([CH3:11])([CH3:12])[CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 53251507HCID 53251507, compound

Product 1

HCID 58456256HCID 58456256, compoundYield 83%

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 ethanol (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 extracted with ethyl acetate (3×) and washed with saturated aqueous sodium bicarbonate. Solvent evaporation gave the title compound (88 mg, 0.165 mmol, 83% yield). ESI: [M+H]+ m/z 535.2. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.82 (d, J=4.9, 1H), 7.93 (d, J=9.6, 2H), 7.46 (s, 1H), 7.27 (d, J=4.9, 1H), 7.14 (s, 1H), 4.07 (dt, J=10.8, 17.9, 2H), 2.31 (s, 3H), 2.05 (s, 3H), 1.96-1.78 (m, 3H), 1.65 (m, 2H), 1.18 (m, 3H), 1.09 (s, 3H), 0.97 (s, 3H). rhSYK activity=+++

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customSolvent evaporation

Sources & evidence

ORD record
ord-fa8db40269c64e6ca18cfcc5d27cddf5
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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