Dimethylformamide → HCID 17922711, compound

HRID 1369545Notes

Reaction equation

HRID 1369545 reaction equation
CI.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:13]=2)=[CH:6][C:5]=1[NH:25][C:26](=[O:38])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:28]=1.[C:39](=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:13]=2)=[CH:6][C:5]=1[NH:25][C:26](=[O:38])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([S:34]([CH3:37])(=[O:35])=[O:36])[CH3:39])[CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22291112HCID 22291112, compound

Product 1

HCID 17922711HCID 17922711, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl iodide (0.023 ml) was added to a mixture of N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-methanesulphonylaminobenzamide (0.17 g), caesium carbonate (0.121 g) and DMF (10 ml) and the resultant mixture was stirred and heated to 50° C. for 72 hours. The reaction mixture was poured into water (200 ml). The precipitate was isolated, washed in turn with water and diethyl ether and dried under vacuum at 60° C. There was thus obtained the title compound (0.1 g); m.p. 208-209° C.; NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.0 (s, 3H), 3.18 (t, 4H), 3.75 (t, 4H), 7.13 (m, 1H), 7.23 (d, 1H), 7.36 (m, 2H), 7.45 (d, 1H), 7.59 (m, 3H), 7.81 (d, 1H), 7.91 (d, 1H), 7.99 (d, 1H), 9.98 (s, 1H), 10.12 (s, 1H); Mass Spectrum: M+H+523.

Workup

  1. customThe precipitate was isolated
  2. washwashed in turn with water and diethyl ether
  3. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-849b05e9453c4455a1973b4a765a1fed
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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