Trifluoroacetic acid → HCID 58456108, compound

HRID 410630Notes

Reaction equation

HRID 410630 reaction equation
[OH:1][C:2]1([C:6]2[S:7][C:8]([C:11]3[CH:12]=[C:13]([NH:18][C:19]4[N:24]=[C:23]([O:25][C:26]([CH3:35])([CH3:34])[C:27]([O:29]C(C)(C)C)=[O:28])[CH:22]=[CH:21][N:20]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:1][C:2]1([C:6]2[S:7][C:8]([C:11]3[CH:12]=[C:13]([NH:18][C:19]4[N:24]=[C:23]([O:25][C:26]([CH3:35])([CH3:34])[C:27]([OH:29])=[O:28])[CH:22]=[CH:21][N:20]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67430361HCID 67430361, compound

Product 1

HCID 58456108HCID 58456108, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-{[2-({3-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}amino)-pyrimidin-4-yl]oxy}-2-methylpropanoate (Example 94A-25, 140 mg, 0.28 mmol) in DCM (1 mL) was added of trifluoroacetic acid (220 μL, 2.8 mmol). The mixture was aged for 2 hours and additional trifluoroacetic acid (500 μL, 6.4 mmol) was added. The reaction was stirred overnight. The reaction was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, filtered and solvent removed under reduced pressure to afford 2-{[2-({3-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}amino)pyrimidin-4-yl]oxy}-2-methylpropanoic acid (110 mg, 0.25 mmol, 88%) as pale yellow oil. MS ESI: [M+H]+ m/z 441.2. 1H NMR (600 MHz, DMSO-d6): δ 9.50 (s, 1H); 8.18 (d, J=6 Hz, 1H); 7.96 (s, 1H); 7.66 (s, 1H); 7.44 (s, 1H); 7.05 (s, 1H); 6.27 (d, J=6 Hz, 1H); 2.52-2.27 (m, 4H); 2.46 (s, 3H); 1.86 (s, 2H); 1.66 (s, 6H). rhSYK activity=++

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-275dfda8834f41ce9d52ad0bd6851c6e
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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