Hydrochloric Acid → HCID 178428303, compound

HRID 928138Notes

Reaction equation

HRID 928138 reaction equation
[F:1][C:2]([C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35]CCCC)=[O:34])[CH2:29][CH2:28]1)([C:4]1[S:5][C:6]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:12]=[C:11]([CH3:26])[CH:10]=2)=[CH:7][N:8]=1)[CH3:3].[OH-].[Na+].Cl>CO.O.C(OCC)(=O)C>[F:1][C:2]([C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]1)([C:4]1[S:5][C:6]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:12]=[C:11]([CH3:26])[CH:10]=2)=[CH:7][N:8]=1)[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178451144HCID 178451144, compound

Product 1

HCID 178428303HCID 178428303, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of butyl trans-4-{1-fluoro-1-[5-(3-methyl-5-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylate (80 mg, 0.14 mmol) in methanol (1.5 mL) was added sodium hydroxide (1.0 M in H2O, 0.28 mL, 0.28 mmol) and the reaction was heated to 60° C. overnight. Then, the reaction was cooled to room temperature, acidified to a pH of ˜3 with HCl (1.0 M in water) and diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford racemic trans-4-{1-fluoro-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylic acid. MS ESI calc'd. for C24H25F4N4O2S [M+H]+ 509. found 509. 1H NMR (500 MHz, DMSO-d6) 12.01 (s, 1H), 10.28 (s, 1H), 8.84 (d, J=4.8, 1H), 8.07 (d, J=3.3, 1H), 8.02 (s, 1H), 7.47 (s, 1H), 7.29 (d, J=4.9, 1H), 7.19 (s, 1H), 2.32 (s, 3H), 2.16-2.01 (m, 1H), 2.00-1.87 (m, 4H), 1.85 (s, 1H), 1.67 (s, 3H), 1.35-1.19 (m, 4H).

Workup

  1. temperatureThen, the reaction was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2db8e371f8654b6a9414c976a4cee0ee
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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