Trifluoroacetic acid → HCID 70657071, compound

HRID 872632Notes

Reaction equation

HRID 872632 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]([CH:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[S:24][CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(O)(C(F)(F)F)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O.O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[S:24][CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70654127HCID 70654127, compound

Product 1

HCID 70657071HCID 70657071, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18672661HCID 18672661, compoundSolvent

Procedure

(S)-tert-butyl 4-(4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)thiazol-2-yl)piperidine-1-carboxylate (0.3 g, 0.540 mmol) and TFA (0.768 g, 6.73 mmol) was dissolved in a mixture of DCM/TFA/H2O and stirred overnight. The reaction mixture was diluted with DCM, washed with saturated Na2CO3 and with water. The organic layer was evaporated. Yield 82%. 1H-NMR (400 MHz; DMSO-d6): δ 1.24 (d, 3H), 1.52 (dd, 1H), 1.58 (dd, 1H), 1.91-1.97 (m, 2H), 2.54-2.62 (m, 2H), 2.97-3.03 (d, 2H), 3.04-3.11 (m, 1H), 4.33 (dd, 1H), 4.41 (dd, 1H), 4.44-4.51 (m, 1H), 6.96 (d, 1H), 7.85 (d, 1H), 7.94 (dd, 1H), 7.99 (d, 1H), 8.07 (d, 1H), 8.08 (s, 1H), 8.28 (d, 1H).

Workup

  1. washwashed with saturated Na2CO3 and with water
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-f48751f5c973410c8f316224ba9ec3fd
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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