Dicyclohexylcarbodiimide → HCID 21963707, compound

HRID 2212190Notes

Reaction equation

HRID 2212190 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8](=[O:18])[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=1[C:27]1[C:31]([C:32](O)=[O:33])=[C:30]([CH3:35])[O:29][N:28]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>C1COCC1>[C:12]1([CH2:11][CH2:10][CH2:9][C:8]([N:4]2[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:32]([C:31]3[C:27]([C:21]4[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:20]=4[Cl:19])=[N:28][O:29][C:30]=3[CH3:35])=[O:33])[CH2:3]2)=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 775203-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylic acidHCID 21963729HCID 21963729, compound

Product 1

HCID 21963707HCID 21963707, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 1-(3-amino-piperidin-1-yl)-4-phenyl-butan-1-one (250 mg, 1.02 mmol) with 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylic acid (260 mg, 1.02 mmol), 1.3-dicyclohexylcarbodiimide (209 mg, 1.01 mmol) and 1-hydroxybenzotriazole (138 mg, 1.02 mmol) in THF and stir overnight at room temperature. Concentrate and elute over silica gel using THF/dichloromethane to give the desired product (326 mg, 66%). MS(ES): (M+1)+ 484.1, 486.1 m/z.

Workup

  1. concentrationConcentrate
  2. washelute over silica gel

Sources & evidence

ORD record
ord-42e015bfc14e4d938b2e6d6eefbd080f
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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