Trifluoroacetic acid → HCID 118216573, compound

HRID 595288Notes

Reaction equation

HRID 595288 reaction equation
C(O)(C(F)(F)F)=O.[OH:8][C:9]1([CH2:22][N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[C:32]([NH:34][C:35]4[N:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][N:36]=4)[CH:31]=[C:30]([CH3:45])[CH:29]=3)[CH:25]=[N:24]2)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1>ClCCl>[CH3:45][C:30]1[CH:29]=[C:28]([C:26]2[CH:25]=[N:24][N:23]([CH2:22][C:9]3([OH:8])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[CH:27]=2)[CH:33]=[C:32]([NH:34][C:35]2[N:40]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:38]=[CH:37][N:36]=2)[CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 118208969HCID 118208969, compound

Product 1

HCID 118216573HCID 118216573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL 1.298 mmol) was added to the solution of racemic tert-butyl 4-hydroxy-4-((4-(3-methyl-5-((4-(trifluoromethyl) pyrimidin-2-yl)amino)phenyl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate (120 mg, 0.23 mmol) in dichloromethane (1 mL). The mixture was stirred at room temperature for 2 days. Additional TFA (0.2 mL) was added and the mixture was stirred for 16 hours. The mixture was purified on reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford 4-((4-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)-1H-pyrazol-1-yl)methyl)piperidin-4-ol. MS ESI calc'd for C21H24F3N6O [M+H]+433. found 433. 1H NMR (500 MHz, CD3OD) δ 8.65 (d, J=4.8, 1H), 7.96 (s, 1H), 7.86 (s, 1H), 7.83 (s, 1H), 7.31 (s, 1H), 7.06 (s, 1H), 7.05 (d, J=4.2, 1H), 4.20 (s, 2H), 3.31-3.17 (m, 4H), 2.33 (s, 3H), 1.94-1.78 (m, 2H), 1.73-1.65 (m, 2H).

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. customThe mixture was purified on reverse phase HPLC (ACN/water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-6897d5405ab74f639b165cb84458c869
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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