4-Bromobutyric acid → 4-(4-Cyano-4-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-piperidin-1-yl)-butyric acid

HRID 2229370Notes

Reaction equation

HRID 2229370 reaction equation
Cl.[C:2]([C:4]1([NH:10][C:11]([CH:13]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:12])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].Br[CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:2]([C:4]1([NH:10][C:11](=[O:12])[CH:13]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])[CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:5][CH2:6][N:7]([CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH2:8][CH2:9]1)#[N:3]

Participants

5

Reactant 3

HCID 758094-Bromobutyric acidHCID 81531DiisopropylethylamineHCID 22260409Morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride

Product 1

HCID 220631154-(4-Cyano-4-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-piperidin-1-yl)-butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared from morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride and 4-bromo-butyric acid in the presence of a hindered tertiary amine base such as Hunig's base in a solvent such as methylene chloride.

Sources & evidence

ORD record
ord-07e4b27c907f42eaab8531e272384fb9
Source dataset
uspto-grants-2002_07
Patent number
US06420364B1

Reaction notes

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