Morpholine → HCID 57479065, compound

HRID 556466Notes

Reaction equation

HRID 556466 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][C:12]2([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:22])[CH:3]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.CCN=C=NCCCN(C)C.Cl>ClCCl>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)([NH:11][C:4]3[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=3[C:6]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:7])[C:13](=[O:22])[NH:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57479064HCID 57479064, compound

Product 1

HCID 57479065HCID 57479065, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 4-chloro-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid (23 mg, 0.05 mmol), morpholine (26 mg, 0.3 mmol) and EDCl (15 mg, 0.08 mmol) in dichloromethane (1 mL) was stirred at room temperature for overnight. The crude was then purified with chromatography to give 22 mg of rac-6-chloro-3-(3-chloro-benzyl)-3-[5-chloro-2-(morpholine-4-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one as a white solid. MS: [M+H]+=530.

Workup

  1. customThe crude was then purified with chromatography

Sources & evidence

ORD record
ord-34cca2896a7d4db5b4f8be990238d76a
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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