Hydrochloric Acid → 2-Methyl-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanoic acid

HRID 1040103Notes

Reaction equation

HRID 1040103 reaction equation
[CH3:1][C:2]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[C:20]([NH:22][C:23]3[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)[CH:19]=[C:18]([CH3:33])[CH:17]=2)=[CH:14][N:15]=1)([CH3:10])[C:3]([O:5]C(C)(C)C)=[O:4].Cl>O1CCOCC1.CCOCC>[CH3:10][C:2]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[C:20]([NH:22][C:23]3[N:28]=[C:27]([C:29]([F:31])([F:32])[F:30])[CH:26]=[CH:25][N:24]=3)[CH:19]=[C:18]([CH3:33])[CH:17]=2)=[CH:14][N:15]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58456207tert-Butyl 2-methyl-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]propanoate

Product 1

HCID 672489222-Methyl-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanoic acidYield 106.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-methyl-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]propanoate (400 mg, 0.836 mmol) was taken up in dioxane (8 mL) before adding HCl (4 M in dioxane, 16 mL, 64.0 mmol). The reaction was stirred at room temperature for 4 d (became yellow suspension over time). The yellow suspension was diluted with Et2O and filtered to isolate 2-methyl-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propanoic acid (HCl salt, 375 mg, 98%) as a yellow solid. MS ESI: [M+H]+ m/z 423.0.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-6a9fbc740d9c48c3874240be372d7869
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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