Dichloromethane → n-(5-Chloropyridin-2-yl)-2-[[1-(1-isopropylpiperidin-4-yl)ethyl]amino]-4-methoxycarbonylbenzamide trihydrochloride

HRID 988715Notes

Reaction equation

HRID 988715 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].C(OC([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][CH:36]=O)[CH2:31][CH2:30]1)=O)(C)(C)C.CCO[C:41]([CH3:43])=O.[CH2:44](Cl)[Cl:45]>>[ClH:13].[ClH:45].[ClH:13].[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:14]=[CH:15][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:17][C:2]=2[NH:1][CH:35]([CH:32]2[CH2:33][CH2:34][N:29]([CH:41]([CH3:43])[CH3:44])[CH2:30][CH2:31]2)[CH3:36])=[N:8][CH:9]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateHCID 219063182-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

Product 1

HCID 21906269n-(5-Chloropyridin-2-yl)-2-[[1-(1-isopropylpiperidin-4-yl)ethyl]amino]-4-methoxycarbonylbenzamide trihydrochlorideYield 61%

Procedure

Using a similar procedure to that described in Example 47-C, 2-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide (2.7 g, 8.8 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-acetaldehyde (3.0 g, 13 mmol) afforded, after trituration with EtOAc:methylene chloride, 2.8 g (61%) of the title compound.

Workup

  1. customafforded

Sources & evidence

ORD record
ord-5822396de616434d988ab97a2d8a5594
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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