Dichloromethane → 1-Methyl-3-(1-{3-[3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propyl}-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one

HRID 1371004Notes

Reaction equation

HRID 1371004 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH:33]([N:36]4[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[N:38]([CH3:45])[C:37]4=[O:46])[CH2:32][CH2:31]3)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(Cl)Cl>FC(F)(F)C(O)=O>[CH3:45][N:38]1[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N:36]([CH:33]2[CH2:34][CH2:35][N:30]([CH2:29][CH2:28][CH2:27][N:14]3[C:11]4[CH2:12][CH2:13][NH:8][CH2:9][C:10]=4[C:16]([C:17]4[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=4)=[N:15]3)[CH2:31][CH2:32]2)[C:37]1=[O:46]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 691598171-{3-[4-(3-Methyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-propyl}-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 222937351-Methyl-3-(1-{3-[3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propyl}-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-{3-[4-(3-Methyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-propyl}-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (1.19 g, 1.86 mmol) was dissolved in trifluoroacetic acid (5 mL) and CH2Cl2 (5 mL) and allowed to stir at room temperature for 2 h. The reaction mixture was concentrated, diluted with CH2Cl2, and washed with saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to afford 1-methyl-3-(1-{3-[3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propyl}-piperidin4-yl)-1,3-dihydro-benzoimidazol-2-one (0.955 g, 96%) as a white foam. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.19. MS (electrospray) calculated for C29H33F3N6O, 539.3 ([M+H]+), m/z found, 539.3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c206c43ddd6473e851a81e9671be326
Source dataset
uspto-grants-2003_06
Patent number
US06583155B2

Reaction notes

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