4-Methylmorpholine → 3-Bromo-4-methoxy-N-(2-methyl-4-morpholin-4-yl-phenyl)-benzamide

HRID 1678528Notes

Reaction equation

HRID 1678528 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.[CH3:13][C:14]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[CH:16][C:15]=1[NH2:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:26][C:15]1[CH:16]=[CH:17][C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:19][C:14]=1[CH3:13])=[O:7]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 668363-Bromo-4-methoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 219550002-Methyl-4-(morpholin-4-yl)aniline

Product 1

HCID 673739843-Bromo-4-methoxy-N-(2-methyl-4-morpholin-4-yl-phenyl)-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-4-methoxy-benzoic acid (247 mg), 2-methyl-4-morpholin-4-yl-phenylamine (205 mg), EDAC (410 mg), HOBT (289 mg) and N-methylmorpholine (353 μl) in DMF (5 ml) was stirred at room temperature for 18 h. The mixture was then diluted with water (30 ml) and the resulting solid collected by filtration and dried (464 mg)

Workup

  1. filtrationthe resulting solid collected by filtration
  2. customdried (464 mg)

Sources & evidence

ORD record
ord-21db227fd8794c53975053a0beeb9e4c
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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