1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68680262, compound

HRID 1765020Notes

Reaction equation

HRID 1765020 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C@@H:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C[N:17](C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.[Cl:37][C:38]1[C:39](=[S:47](=[O:49])=[O:48])[CH2:40][C:41](=[CH:45][CH:46]=1)[C:42](O)=[O:43]>>[NH2:17][S:47]([C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:38]=1[Cl:37])[C:42]([NH:14][C@H:7]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:2]1[CH3:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:43])(=[O:49])=[O:48]

Participants

5

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53445303HCID 53445303, compoundHCID 68681705HCID 68681705, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 68680262HCID 68680262, compoundYield 46.7%

Procedure

According to the procedure described in Example 2, starting with 0.12 g (0.63 mmol) of [(S)-[(2S)-(1-methyl-2-pyrrolidinyl)]phenylmethyl]amine, 0.12 g (0.63 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 0.085 g (0.63 mmol) of hydroxybenzotriazole and 0.14 g (0.63 mmol) of 4-chloro-3-sulfonylbenzoic acid, and after work-up and purification by chromatography on silica gel with a gradient of dichloromethane and methanol, 0.12 g of 3-(aminosulfonyl)-4-chloro-N-[(S)-[(2S)-1-methyl-2-pyrrolidinyl](phenyl)methyl]benzamide is obtained.

Workup

  1. customafter work-up and purification by chromatography on silica gel with a gradient of dichloromethane and methanol

Sources & evidence

ORD record
ord-b04ecfeac71e4fedabc97f5484053a50
Source dataset
uspto-grants-2007_06
Patent number
US07226917B2

Reaction notes

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