Dichloromethane → HCID 86584252, compound

HRID 2288219Notes

Reaction equation

HRID 2288219 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7].[CH3:33][N:34]1[CH:38]=[C:37]([CH:39]=O)[CH:36]=[N:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:55]CCl>>[ClH:55].[F:30][C:27]([F:28])([F:29])[C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:39][C:37]2[CH:36]=[N:35][N:34]([CH3:33])[CH:38]=2)[CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

Product 1

HCID 86584252HCID 86584252, compound

Procedure

to a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (0.2 g) and 1-methyl-4-formyl-1H-pyrazole (0.05 g) in dichloromethane (2 ml) under nitrogen atmosphere was added sodium triacetoxyborohydride (151 mg) at room temperature. After 4 hours, the reaction mixture was evaporated under reduced pressure, and ethyl acetate (20 ml) and aqueous sodium hydrogen carbonate solution (10 ml) were added to the residue. The organic layer was separated and washed wit brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and methanol (50:1). The obtained product was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[(1-methyl-1H-pyrazol-4-yl)methyl]piperazine hydrochloride (154 mg).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure, and ethyl acetate (20 ml) and aqueous sodium hydrogen carbonate solution (10 ml)
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed wit brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel using
  8. additiona mixture of ethyl acetate and methanol (50:1)
  9. dissolutionThe obtained product was dissolved in ethyl acetate
  10. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-35346b6100e749c5bcaad188797f32ab
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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