Dicyclohexylcarbodiimide → HCID 178495790, compound

HRID 1268908Notes

Reaction equation

HRID 1268908 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)[N:10]=1)([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:53][O:54][CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][CH:60]([C:63](O)=[O:64])[CH2:59][CH2:58]1>CN(C=O)C.ClCCl>[CH3:4][C:3]([C:6]1[NH:10][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)=[C:8]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[N:7]=1)([CH3:5])[CH2:2][NH:1][C:63]([CH:60]1[CH2:59][CH2:58][N:57]([CH2:56][CH2:55][O:54][CH3:53])[CH2:62][CH2:61]1)=[O:64]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 184469145-[2-(2-Amino-1,1-dimethyl-ethyl)-5-pyridin-4-yl-1H-imidazol-4-yl]-indan-1-oneHCID 450750321-(2-Methoxyethyl)piperidine-4-carboxylic acid hydrochloride

Product 1

HCID 178495790HCID 178495790, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 1, Step 6 (0.1 g, 0.29 mmol), 1-hydroxybenzotriazole (0.06 g, 0.44 mmol) and polymer bound 1,3-dicyclohexylcarbodiimide (0.4 g, 0.6 mmol, 1.52 mmol/g) in a 1:1 mixture of dichloromethane and DMF (4 ml) was stirred at room temperature for 30 min. A solution of 1-(2-methoxy-ethyl)-piperidine-4-carboxylic acid hydrochloride [WO 97/25309] (0.098 g, 0.44 mmol) in DMF (2 ml) was then added and the mixture stirred at room temperature overnight. The reaction mixture was then filtered, the solvent removed in vacuo and the crude residue purified by silica gel chromatography eluting with a 1:9:90 mixture of 0.88 ammonia solution:methanol:dichloromethane to give the title compound (0.12 g, 80%) as a yellow oil; MS(AP+) m/e 516 [M+H]+.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. filtrationThe reaction mixture was then filtered
  3. customthe solvent removed in vacuo
  4. customthe crude residue purified by silica gel chromatography
  5. washeluting with a 1:9:90 mixture of 0.88 ammonia solution

Sources & evidence

ORD record
ord-9785d6c1b4f84b7da16d686ef341d29b
Source dataset
uspto-grants-2007_04
Patent number
US07199137B2

Reaction notes

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