Ethyl (morpholin-4-ylcarbonothioyl)carbamate → {[1-(4-Cyano-1-propyl-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethylimino]-morpholin-4-yl-methyl}-carbamic acid ethyl ester

HRID 2085033Notes

Reaction equation

HRID 2085033 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=S)[CH3:2].Cl.Cl.[NH2:17][CH:18]([CH2:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:19]([NH:21][C:22]1([C:31]#[N:32])[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]1)=[O:20]>>[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6](=[N:17][CH:18]([C:19](=[O:20])[NH:21][C:22]1([C:31]#[N:32])[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][CH3:30])[CH2:26][CH2:27]1)[CH2:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH3:2]

Participants

3

Reactant 2

HCID 2824559Ethyl (morpholin-4-ylcarbonothioyl)carbamateHCID 865852002-amino-N-(-4-cyano-1-propyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride salt

Product 1

HCID 22091416{[1-(4-Cyano-1-propyl-piperidin-4-ylcarbamoyl)-2-cyclohexyl-ethylimino]-morpholin-4-yl-methyl}-carbamic acid ethyl ester

Procedure

The title compound was prepared starting from (morpholine-4-carbothioyl)-carbamic acid ethyl ester and 2-amino-N-(-4-cyano-1-propyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride salt according to the procedure from Example 5, step b, except that the compound was first purified by chromatography over silica gel using 9:1 methylene chloride:methanol as the eluant prior to reverse phase HPLC purification. MS, m/z 505=M+1.

Workup

  1. customwas first purified by chromatography over silica gel using 9:1 methylene chloride
  2. customphase HPLC purification

Sources & evidence

ORD record
ord-c1679cff45a84e5b89e032ae91cfc801
Source dataset
uspto-grants-2004_04
Patent number
US06720319B2

Reaction notes

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