1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-amino-5-chloro-2-methoxy-N-((4-methoxy-1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamide

HRID 344535Notes

Reaction equation

HRID 344535 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1([O:24][CH3:25])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:7][CH2:6]1.[NH2:26][C:27]1[C:35]([Cl:36])=[CH:34][C:30]([C:31](O)=[O:32])=[C:29]([O:37][CH3:38])[CH:28]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>C(N(CC)CC)C>[NH2:26][C:27]1[C:35]([Cl:36])=[CH:34][C:30]([C:31]([NH:3][CH2:4][C:5]2([O:24][CH3:25])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:7][CH2:6]2)=[O:32])=[C:29]([O:37][CH3:38])[CH:28]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 700750634-Aminomethyl-4-methoxy-1-(4-phenylsulfonylbutyl)piperidine dihydrochloride

Product 1

HCID 538047524-amino-5-chloro-2-methoxy-N-((4-methoxy-1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Aminomethyl-4-methoxy-1-(4-phenylsulfonylbutyl)piperidine dihydrochloride (2.2 g) as starting compound, triethylamine (2.2 ml), 4-amino-5-chloro-2-methoxybenzoic acid (1.07 g), 1-hydroxybenzotriazole (0.75 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.07 g) were reacted and treated in the same manner as in Example 270 to give 1.44 g of 4-amino-5-chloro-2-methoxy-N-((4-methoxy-1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamide.

Workup

  1. customwere reacted
  2. additiontreated in the same manner as in Example 270

Sources & evidence

ORD record
ord-a8d6bd453cb046bf8f6c5bfa5ea43fc8
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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