Methanesulfonamide → HCID 89498260, compound

HRID 1430281Notes

Reaction equation

HRID 1430281 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29](O)=[O:30])[C:26]([C:32]3[CH:33]=[N:34][N:35]([CH2:38][C:39]4([CH2:46][CH2:47][O:48][CH3:49])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[C:36]=3[CH3:37])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].[CH3:50][S:51]([NH2:54])(=[O:53])=[O:52].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[CH:24]=[CH:25][C:26]([C:32]3[CH:33]=[N:34][N:35]([CH2:38][C:39]4([CH2:46][CH2:47][O:48][CH3:49])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]4)[C:36]=3[CH3:37])=[C:27]([C:29](=[O:30])[NH:54][S:51]([CH3:50])(=[O:53])=[O:52])[N:28]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89498274HCID 89498274, compound

Product 1

HCID 89498260HCID 89498260, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 134G (50 mg) in dichloromethane (2 mL) was added methanesulfonamide (7.4 mg), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (28 mg) and 4-dimethylaminopyridine (18 mg). The mixture was stirred overnight. The mixture was loaded on a silica gel column and eluted with 5% methanol in dichloromethane to give the pure product. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 8.03 (d, 1H), 7.79 (d, 1H), 7.60 (s, 1H), 7.41 (m, 5H), 7.30 (s, 1H), 7.00 (d, 1H), 4.96 (s, 2H), 3.94 (m, 2H), 3.83 (s, 2H), 3.42 (t, 2H), 3.41 (s, 3H), 3.27 (s, 3H), 3.21 (m, 3H), 3.11 (m, 2H), 2.12 (s, 3H), 1.45 (m, 16H)

Workup

  1. washeluted with 5% methanol in dichloromethane
  2. customto give the pure product

Sources & evidence

ORD record
ord-71a349e40da741b5a96dd86588092ee0
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

Loading…