(Pyrazin-2-yl)methanamine → 4-(3-Phenyl-indole-1-sulfonyl)-N-pyrazin-2-ylmethyl-benzamide

HRID 737033Notes

Reaction equation

HRID 737033 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[N:40]1[CH:45]=[CH:44][N:43]=[CH:42][C:41]=1[CH2:46][NH2:47]>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH:47][CH2:46][C:41]4[CH:42]=[N:43][CH:44]=[CH:45][N:40]=4)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 266781(Pyrazin-2-yl)methanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 589751414-(3-Phenyl-indole-1-sulfonyl)-benzoic acid

Product 1

HCID 589752274-(3-Phenyl-indole-1-sulfonyl)-N-pyrazin-2-ylmethyl-benzamideYield 20.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Add 10 ml dry DMF to a flask under N2 containing 4-(3-Phenyl-indole-1-sulfonyl)-benzoic acid (500 mg, 1.33 mmol, 1.0 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (279 mg, 1.46 mmol, 1.1 eq), Dimethyl-pyridin-4-yl-amine (16 mg, 0.132 mmol, 0.1 eq), and C-Pyrazin-2-yl-methylamine (217 mg, 1.99 mmol, 1.5 eq). Stir for 18 hours at room temperature. Remove solvent on rotovap and purify by silica gel chromatography to give 4-(3-Phenyl-indole-1-sulfonyl)-N-pyrazin-2-ylmethyl-benzamide (127 mg, 20% yield). Mass Spectrum (m/e): 468.95 (MH+).

Workup

  1. customRemove solvent on rotovap and purify by silica gel chromatography

Sources & evidence

ORD record
ord-cda7b4fd73be4270bcf0fb89c043ed00
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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