1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 54490953, compound

HRID 2288199Notes

Reaction equation

HRID 2288199 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:7].Cl.[CH2:44]([NH:46][CH2:47][CH3:48])[CH3:45].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>ClCCl>[F:42][C:2]([F:41])([F:1])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:36]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:46]([CH2:47][CH3:48])[CH2:44][CH3:45])=[O:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:7]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 10197650Diethylammonium chlorideHCID 54441405HCID 54441405, compound

Product 1

HCID 54490953HCID 54490953, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-carboxybenzyl)-2-(1H-indol-3-ylmethyl)piperazine (150 mg) and diethylamine hydrochloride (28 mg) in dry dichloromethane (5 ml) were added a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (40 mg) in dichloromethane (1ml) and 1-hydroxybenzotriazole (34 mg) at room temperature. After 5 hours, the reaction mixture was poured into aqueous sodium bicarbonate solution (20 ml). The organic layer was separated and washed with brine and dried over magnesium sulfate. The crude product obtained was purified by column chromatography on silica gel using ethyl acetate-n-hexane (4:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(N,N-diethylaminocarbonyl)benzyl]-2-(1H-indol-3-ylmethyl)piperazine (107 mg) as a powder.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product obtained
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f686deee08e0441cad91209e8cfb6bb2
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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