2-Methylbenzenesulfonamide → HCID 14882638, compound

HRID 330195Notes

Reaction equation

HRID 330195 reaction equation
[CH2:1]([NH:5][C:6]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[O:7])[CH2:2][CH2:3][CH3:4].Cl.CN(C)CCCN=C=NCC.[CH3:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[S:50]([NH2:53])(=[O:52])=[O:51]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([NH:5][C:6]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:53][S:50]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[CH3:43])(=[O:52])=[O:51])=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882657HCID 14882657, compound

Product 1

HCID 14882638HCID 14882638, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[5-(butylcarbamoyl)methyl-1-methylindol-3-ylmethyl]-3-methoxybenzoic acid (0.18 g), 4-(dimethylamino)pyridine (0.06 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.10 g), and 2-methylbenzenesulfonamide (0.08 g) in methylene chloride (3 ml) was stirred under a nitrogen atmosphere for 36 hr. The mixture was diluted with methylene chloride; washed (10% v/v hydrochloric acid, water), evaporated and dried under vacuum to give the title compound (0.21 g, 86%) as a pale pink powder: mp 108°-110°.

Workup

  1. washwashed (10% v/v hydrochloric acid, water)
  2. customevaporated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3a74a27918ec4137b0eb1c100ad20aa2
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…