Dicyclohexylcarbodiimide → HCID 14697224, compound

HRID 2073170Notes

Reaction equation

HRID 2073170 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=2)[C:6]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[Cl:29].[C:30]([O:34][C:35]([N:37]([CH2:41][CH:42]([OH:57])[CH2:43][O:44][C:45]1[CH:53]=[CH:52][CH:51]=[C:50]2[C:46]=1[CH:47]=[C:48]([C:54](O)=[O:55])[NH:49]2)[CH:38]([CH3:40])[CH3:39])=[O:36])([CH3:33])([CH3:32])[CH3:31].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:30]([O:34][C:35]([N:37]([CH2:41][CH:42]([OH:57])[CH2:43][O:44][C:45]1[CH:53]=[CH:52][CH:51]=[C:50]2[C:46]=1[CH:47]=[C:48]([C:54]([NH:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]([O:23][CH3:24])=[O:22])=[CH:13][CH:14]=3)[C:6]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[Cl:29])=[O:55])[NH:49]2)[CH:38]([CH3:39])[CH3:40])=[O:36])([CH3:32])([CH3:33])[CH3:31]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13997124HCID 13997124, compoundHCID 14697223HCID 14697223, compound

Product 1

HCID 14697224HCID 14697224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Aminomethyl-2-n-butyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloroimidazole (prepared by the procedure of Example 148, Part C, in EP No. 0253310) (0.71 g, 1.7 mmol), 1 eq), 4-[3-(N-t-butoxycarbonyl-N-isopropylamino)-2-hydroxypropoxy]indole-2-carboxylic acid (prepared by the procedure of Example 1, Part g, in EPO No. 174162) (0.84 g, 1.7 mmol, 1 eq), 1-hydroxybenzotriazole (0.24 g, 1.8 mmol, 1.05 eq), dicyclohexylcarbodiimide (0.37 g, 1.8 mmol, 1.05 eg) and DMF (25 mL) were mixed at 0° C. and left in the refrigerator for 4 days at that temperature. The dicyclohexylurea was filtered off and the mixture concentrated and chromatographed in 1:1 hexane/ethyl acetate yielding 970 mg of a white solid; mp 157.5°-160° C.

Workup

  1. filtrationThe dicyclohexylurea was filtered off
  2. concentrationthe mixture concentrated
  3. customchromatographed in 1:1 hexane/ethyl acetate yielding 970 mg of a white solid

Sources & evidence

ORD record
ord-4cb333b1ca1d488daa95d60178356cbb
Source dataset
uspto-grants-1990_04
Patent number
US04916129

Reaction notes

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