Trifluoroacetic acid → HCID 58456358, compound

HRID 410617Notes

Reaction equation

HRID 410617 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58456281HCID 58456281, compound

Product 1

HCID 58456358HCID 58456358, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclopropanecarboxylate (375 mg, 0.787 mmol) was taken up in CH2Cl2 (12 mL) before adding TFA (3 mL). The reaction was stirred at room temperature overnight. The reaction was evaporated to dryness, and the residue was azeotroped with DCE (3×) to provide 1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclopropanecarboxylic acid (TFA salt) (421 mg, 100%) as a yellow solid. MS ESI: [M+H]+ m/z 421.0. 1H NMR (600 MHz, DMSO-d6) δ 13.15 (s, 1H), 10.21 (s, 1H), 8.80 (d, J=4.8, 1H), 7.95 (s, 1H), 7.87 (s, 1H), 7.44 (s, 1H), 7.25 (d, J=4.9, 1H), 7.12 (s, 1H), 2.29 (s, 3H), 1.81-1.62 (m, 4H). rhSYK activity=+++

Workup

  1. customThe reaction was evaporated to dryness
  2. customthe residue was azeotroped with DCE (3×)

Sources & evidence

ORD record
ord-512774319f8a4658bfdd1cbb4601a716
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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