Morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride → Morpholine-4-carboxylic acid {1-[4-cyano-1-(2-dimethylamino-acetyl)-piperidin-4-ylcarbamoyl]-2-cyclohexyl-ethyl}-amide

HRID 2229358Notes

Reaction equation

HRID 2229358 reaction equation
CNN(NC)CC(O)=O.Cl.[C:11]([C:13]1([NH:19][C:20]([CH:22]([NH:30][C:31]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:32])[CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:21])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)#[N:12].C(C1(NC(C(N[C:69]([N:71]2[CH2:76]C[O:74][CH2:73][CH2:72]2)=O)CC(C)(C)C)=O)CC(C2C=CC=CC=2)NC(C2C=CC=CC=2)C1)#N>>[C:11]([C:13]1([NH:19][C:20]([CH:22]([NH:30][C:31]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:32])[CH2:23][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:21])[CH2:14][CH2:15][N:16]([C:73](=[O:74])[CH2:72][N:71]([CH3:76])[CH3:69])[CH2:17][CH2:18]1)#[N:12]

Participants

4

Reactant 3

HCID 22260409Morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochlorideHCID 22260506Morpholine-4-carboxylic acid [1-(4-cyano-2,6-diphenyl-piperidin-4-ylcarbamoyl)-3,3-dimethyl-butyl]-amideHCID 86760541n,n-Dimethylaminoglycine

Product 1

HCID 22260588Morpholine-4-carboxylic acid {1-[4-cyano-1-(2-dimethylamino-acetyl)-piperidin-4-ylcarbamoyl]-2-cyclohexyl-ethyl}-amide

Procedure

The title compound was prepared from N,N-dimethylaminoglycine and morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide hydrochloride using the coupling method described in Example 1-part (d). The product was purified by reverse phase preparative HPLC to give the title compound as an off-white solid; MS, m/z 477=M+1.

Workup

  1. customThe product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-932818edf6454897b20902a8f51cf858
Source dataset
uspto-grants-2002_07
Patent number
US06420364B1

Reaction notes

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