Methanesulfonamide → HCID 89498260, compound

HRID 1778889Notes

Reaction equation

HRID 1778889 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-a536381251a8403085ba50d28b9f28ce
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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