Dichloromethane → HCID 22660821, compound

HRID 392977Notes

Reaction equation

HRID 392977 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:25]3[CH:33]=[CH:34][C:35]([C:37](O)=[O:38])=[CH:36][C:24]=3[N:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClCCl>CN(C)C=O>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:26]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[C:25]3[CH:33]=[CH:34][C:35]([C:37]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:38])=[CH:36][C:24]=3[N:23]=2)=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 491098HCID 491098, compound

Product 1

HCID 22660821HCID 22660821, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonamide (0.0188 g, 0.198 mmol), sodium hydride, and the acid chloride of 49 (0.0083 g, 0.019 mmol) were reacted in dimethylformamide and dichloromethane according to the procedure described for example 8. The crude material was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford the product as a white solid (0.0055 g, 52%). 1H NMR (CDCl3) δ 8.68 (s, 1H), 8.17 (d, 1H, J=8.8 Hz), 7.91 (d, 1H, J=8.8 Hz), 7.69 (d, 2H, J=8.5 Hz), 7.48-7.37 (m, 5H), 7.24 (d, 2H, J=8.7 Hz), 5.18 (s, 2H), 4.57 (m, 1H), 3.34 (s, 3H), 2.34 (br m, 2H), 2.06 (br m, 4H), 1.85 (br m, 1H), 1.39 (br m, 3H); ESI-MS m/e 504.3 (M+1); HPLC purity (ELSD)>95%.

Workup

  1. customThe crude material was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-5fb3c26bd4f147d6aaa9eb9be99ef7e0
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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