Water → HCID 86753901, compound

HRID 1418593Notes

Reaction equation

HRID 1418593 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].[Cl:33][CH2:34][C:35]1[N:36]=[C:37]([NH:40][C:41]([CH2:43][CH2:44][O:45][CH3:46])=[O:42])[S:38][CH:39]=1.C(=O)([O-])O.[Na+].O>CN(C)C=O>[ClH:33].[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]([CH2:34][C:35]2[N:36]=[C:37]([NH:40][C:41](=[O:42])[CH2:43][CH2:44][O:45][CH3:46])[S:38][CH:39]=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

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazineHCID 14129777HCID 14129777, compound

Product 1

HCID 86753901HCID 86753901, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (120 mg), 4-chloromethyl-2-(2-methoxyethylcarbonylamino)thiazole (70 mg) and powdered sodium hydrogen carbonate (27 mg) in dry dimethylformamide was stirred for 5 hours and 20 minutes at 60° C. The reaction mixture was powered into water and the resulting precipitate was collected by filtration. The crude product was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (30:1). The eluate was evaporated under reduced pressure and treated with 17.6% hydrogen chloride in ethanol (0.12 ml) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[[2-(3-methoxypropanoylamino)thiazol-4-yl]methyl]piperazine hydrochloride (140 mg).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude product was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (30:1)
  3. customThe eluate was evaporated under reduced pressure
  4. additiontreated with 17.6% hydrogen chloride in ethanol (0.12 ml)

Sources & evidence

ORD record
ord-38600f82eca240dda4d890e8cf9c5ada
Source dataset
uspto-grants-1999_03
Patent number
US05883098

Reaction notes

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