Methanesulfonamide → 2-[2-[3-(2-benzothiazolylmethoxy)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxy]-N-(methanesulfonyl)acetamide

HRID 1602512Notes

Reaction equation

HRID 1602512 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:42]=[CH:43][CH:44]=1)[C:15]([NH:17][C:18]1[CH:28]=[C:27]([CH2:29][CH2:30][CH2:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:26]=[CH:25][C:19]=1[O:20][CH2:21][C:22](O)=[O:23])=[O:16].[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:42]=[CH:43][CH:44]=1)[C:15]([NH:17][C:18]1[CH:28]=[C:27]([CH2:29][CH2:30][CH2:31][S:32]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH:26]=[CH:25][C:19]=1[O:20][CH2:21][C:22]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:23])=[O:16]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 542101982-[3-(2-Benzothiazolylmethoxy)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid

Product 1

HCID 196114952-[2-[3-(2-benzothiazolylmethoxy)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxy]-N-(methanesulfonyl)acetamideYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[3-(2-benzothiazolylmethoxy)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid (200 mg, 0.31 mmol), methanesulfonamide (31 mg), 4-dimethylaminopyridine (45 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (125 mg) and dichloromethane (10 ml) was stirred at room temperature for 3 days. The reaction solution was washed with 1 N hydrochloric acid, water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. By recrystallizing the resulting solid material from acetonitrile (2 ml), 2-[2-[3-(2-benzothiazolylmethoxy)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxy]-N-(methanesulfonyl)acetamide 0.5 hydrate (70 mg, 0.096 mmol, 31%) was obtained as colorless crystals.

Workup

  1. washThe reaction solution was washed with 1 N hydrochloric acid, water and brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customBy recrystallizing the resulting solid material from acetonitrile (2 ml)

Sources & evidence

ORD record
ord-1cbef0176b2d482e963c3a9cd255e569
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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