HCID 58625813, compound → HCID 178522965, compound

HRID 2116913Notes

Reaction equation

HRID 2116913 reaction equation
[F:1][C:2]([F:56])([F:55])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13](COCC[Si](C)(C)C)[C:12]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:24][CH2:23]3)=[N:11][C:10]=2[C:38]([NH:40][CH2:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][N:43]2C(OC(C)(C)C)=O)=[O:39])=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:43]1[CH2:44][CH2:45][CH2:46][CH2:47][CH:42]1[CH2:41][NH:40][C:38]([C:10]1[N:11]=[C:12]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[C:33]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:31]=[CH:30][N:29]=3)[CH2:24][CH2:23]2)[NH:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:56])([F:1])[F:55])=[CH:4][CH:5]=1)=[O:39]

Participants

3

Reactant 1

HCID 58625813HCID 58625813, compound

Product 1

HCID 178522965HCID 178522965, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 2-((5-(4-(trifluoromethyl)phenyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamido)methyl)piperidine-1-carboxylate from step (a) above (200. mg, 0.247 mmol) in TFA:DCM (4:1) was stirred at RT for 7 min. The solvent was removed and the residue was added H2O (0.5 mL). Then, saturated NaHCO3 was added at 0° C. until pH ˜7 and the solvents were removed. The residue was purified on silica gel using ISCO Combiflash® system with DCM/2M methanolic ammonia gradient to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 582 (M+1).

Workup

  1. customThe solvent was removed
  2. additionthe residue was added H2O (0.5 mL)
  3. additionThen, saturated NaHCO3 was added at 0° C. until pH ˜7
  4. customthe solvents were removed
  5. customThe residue was purified on silica gel using ISCO Combiflash® system with DCM/2M methanolic ammonia gradient

Sources & evidence

ORD record
ord-f89075c0dda24d1dbb8adba809c786d4
Source dataset
uspto-grants-2008_10
Patent number
US07439360B2

Reaction notes

Loading…