Hydrochloric Acid → HCID 66780515, compound

HRID 1958055Notes

Reaction equation

HRID 1958055 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:16]=2[CH3:25])[C:12]2[N:26]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[S:28][C:11]=2[C:10](=[O:35])[N:9]=1)(=O)C.Cl>CO>[OH:6][CH2:7][C:8]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[C:16]=2[CH3:25])[C:12]2[N:26]=[C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[S:28][C:11]=2[C:10](=[O:35])[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66780417HCID 66780417, compound

Product 1

HCID 66780515HCID 66780515, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (0.166 mL, 0.166 mmol) was added to a solution of [4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]methyl acetate (80 mg, 0.166 mmol) in Methanol (1.5 mL). The reaction was stirred at RT for 30 min. 1N HCl was added to adjust to pH=5. The mixture was partitioned between DCM and NaCl solution. The organic layer was concentrated to give the titled compound, 65 mg (90%). LC/MS (ES) m/z 441.0 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.65 (m, 1H), 7.36 (m, 1H), 6.87 (m, 1H), 5.60 (s, 2H), 4.15 (m, 2H), 3.66 (m, 4H), 3.56 (m, 4H), 2.49 (s, 3H)

Workup

  1. customThe mixture was partitioned between DCM and NaCl solution
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-784a6d824561484fa0b501d1a88d2984
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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