Trifluoroacetic acid → HCID 73055446, compound

HRID 1779061Notes

Reaction equation

HRID 1779061 reaction equation
[NH2:1][C:2](=[O:46])[CH2:3][C:4]1[C:41]([C:42]([F:45])([F:44])[F:43])=[CH:40][CH:39]=[CH:38][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[CH2:29][CH2:30][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:10]3[N:9]=[C:8]([CH2:7][CH2:6][C:5]4[CH:38]=[CH:39][CH:40]=[C:41]([C:42]([F:43])([F:44])[F:45])[C:4]=4[CH2:3][C:2]([NH2:1])=[O:46])[C:13]([C:14]([F:17])([F:15])[F:16])=[CH:12][N:11]=3)=[CH:20][CH:21]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712704HCID 86712704, compound

Product 1

HCID 73055446HCID 73055446, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-3-(trifluoromethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A97) (0.075 g, 0.12 mmol) in DCM (5 mL) was added TFA (0.20 mL, 2.6 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The volatiles were evaporated under reduced pressure and the residue partitioned between water (20 mL) and EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (2×20 mL). The combined organic extracts were dried using a phase separation cartridge then the volatiles were removed under reduced pressure. The residue was triturated with Et2O and the resulting precipitate collected by filtration to give the title compound 22 (56 mg, 88%); 1H NMR (400 MHz, d6-DMSO) δ 10.22 (s, 1H), 8.67 (s, 1H), 8.29 (brs, 1H), 7.68 (d, J=8.6 Hz, 2H), 7.57 (d, J=7.9 Hz, 1H), 7.52 (d, J=7.6 Hz, 1H), 7.48 (s, 1H), 7.41 (t, J=7.8 Hz, 1H), 7.19 (d, J=8.6 Hz, 2H), 6.94 (s, 1H), 3.73 (s, 2H), 3.38 (m, 2H), 3.10 (m, 4H), 2.98 (td, J=12.8, 2.6 Hz, 2H), 2.79 (tt, J=11.7, 2.7 Hz, 1H), 1.93 (d, J=15.8 Hz, 2H), 1.74 (qd, J=13.8, 4.0 Hz, 2H). LCMS-A: rt 4.99 min; m/z 552.3 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue partitioned between water (20 mL) and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (2×20 mL)
  5. customThe combined organic extracts were dried
  6. customa phase separation cartridge
  7. customthe volatiles were removed under reduced pressure
  8. customThe residue was triturated with Et2O
  9. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-c6fbca58492e4ff286785ed83a32daea
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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