Dimethylamine, hydrochloride → HCID 67395938, compound

HRID 70638Notes

Reaction equation

HRID 70638 reaction equation
Cl.[CH3:2][NH:3][CH3:4].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[Cl:28][C:29]1[CH:30]=[CH:31][C:32](/[C:37](/[C:45]2[CH:53]=[CH:52][C:48]([C:49](O)=[O:50])=[CH:47][CH:46]=2)=[CH:38]/[C@H:39]2[CH2:43][CH2:42][C:41](=[O:44])[NH:40]2)=[N:33][C:34]=1[O:35][CH3:36]>C(Cl)(Cl)Cl.CN(C)C=O.C(N(CC)CC)C>[Cl:28][C:29]1[CH:30]=[CH:31][C:32](/[C:37](/[C:45]2[CH:46]=[CH:47][C:48]([C:49]([N:3]([CH3:4])[CH3:2])=[O:50])=[CH:52][CH:53]=2)=[CH:38]/[C@H:39]2[CH2:43][CH2:42][C:41](=[O:44])[NH:40]2)=[N:33][C:34]=1[O:35][CH3:36]

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67398344HCID 67398344, compound

Product 1

HCID 67395938HCID 67395938, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Dimethylamine hydrochloride (43 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (121 mg), 1-hydroxybenzotriazole monohydrate (97 mg) and triethylamine were added to a mixed solution of 4-{(E)-1-(5-chloro-6-methoxypyridin-2-yl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}benzoic acid (131 mg) in chloroform and N,N-dimethylformamide (4 mL, 3:1), and the mixture was stirred at room temperature for three hours. The reaction solution was concentrated and the resulting residue was purified by silica gel chromatography (chloroform:methanol=100:0→80:20) to give 4-{(E)-1-(5-chloro-6-methoxypyridin-2-yl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-N,N-dimethylbenzamide as a brown oil (139 mg, 99%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by silica gel chromatography (chloroform:methanol=100:0→80:20)

Sources & evidence

ORD record
ord-cd58211155a0457195b60954f86ee1c0
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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