4-Methylmorpholine → HCID 86643246, compound

HRID 1516542Notes

Reaction equation

HRID 1516542 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH3:19])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[NH2:20].C[C:22]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([C:31]([OH:33])=O)=[CH:30][C:24]=2[N:23]=1.CN1CCO[CH2:37][CH2:36]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH3:19])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[NH:20][C:31]([C:29]1[CH:28]=[CH:27][C:25]2[N:26]([CH2:36][CH3:37])[CH:22]=[N:23][C:24]=2[CH:30]=1)=[O:33]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidHCID 684676422-Methyl-4-[3-(2-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-phenylamine

Product 1

HCID 86643246HCID 86643246, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Methyl-4-[3-(2-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-phenylamine (27 mg, 0.1 mmol) and 2-methyl-1H-benzoimidazole-5-carboxylic acid (17.6 mg, 0.1 mmol) were dissolved in a mixture of 3 ml of dichloromethane and 1 ml of dimethylformamide. To this solution was then added N-methylmorpholine (33 μl, 0.3 mmol), 1-hydroxybenzotriazole (17.6 mg, 0.13 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (22 mg, 0.123 mmol). The reaction was stirred at room temperature for 20 h. Evaporation and RP-HPLC gave 25 mg of the title compound with trifluoro-acetic acid as a salt (46%). MS: 432.5 (M+H)

Workup

  1. customEvaporation and RP-HPLC

Sources & evidence

ORD record
ord-ebf6306fffb743dbaa80f34a1a50a9e5
Source dataset
uspto-grants-2012_07
Patent number
US08227504B2

Reaction notes

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