2-Methylbenzenesulfonamide → HCID 15872196, compound

HRID 1739582Notes

Reaction equation

HRID 1739582 reaction equation
[CH:1]([NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([NH:26][C:27]([O:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:28])=[CH:23][CH:24]=2)[C:19]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][C:37]=2[O:45][CH3:46])=[CH:18]1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[C:59]1([CH3:69])[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=1[S:65]([NH2:68])(=[O:67])=[O:66]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:1]([NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([NH:26][C:27]([O:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[O:28])=[CH:23][CH:24]=2)[C:19]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40]([NH:68][S:65]([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=3[CH3:69])(=[O:67])=[O:66])=[O:41])=[CH:38][C:37]=2[O:45][CH3:46])=[CH:18]1)=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54169572HCID 54169572, compound

Product 1

HCID 15872196HCID 15872196, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[1-(benzhydryl-carbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.50 grams, 0.81 mmol), 4-dimethylaminopyridine (0.015 grams, 1.21 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (0.23 g, 1.21 mmol) in methylene chloride (30 mL) was added o-tolylsulfonamide (0.14 g, 0.81 mmol). The resulting solution was stirred for 12 hours at room temperature. The solution was diluted with methylene chloride and washed with 1 M hydrochloric acid (aq). The organics were dried over magnesium sulfate and concentrated. Chromatography on silica gel (2% methanol/methylene chloride), followed by recrystallization from wet ether gave the titled compound (0.455 grams, 73% yield). m.p.=253-254° C. Anal. calcd. for C44H42N4O7S: C, 68.55; H, 5.49; N, 7.27. Found: C, 69.21; H, 5.54; N, 7.14. HRMS calcd. for C44H42N4O7S: 770.2774. Found 770.2736.

Workup

  1. washwashed with 1 M hydrochloric acid (aq)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customChromatography on silica gel (2% methanol/methylene chloride), followed by recrystallization from wet ether

Sources & evidence

ORD record
ord-af2ad241960f439d98fc18d51aa63018
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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