Pyridine → HCID 22291112, compound

HRID 967903Notes

Reaction equation

HRID 967903 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:16]=2)=[CH:9][C:8]=1[NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH2:36])[CH:31]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[CH:16]=2)=[CH:9][C:8]=1[NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH:36][S:2]([CH3:1])(=[O:4])=[O:3])[CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 22291109HCID 22291109, compound

Product 1

HCID 22291112HCID 22291112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.16 ml) was added to a stirred mixture of N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-aminobenzamide (0.765 g), pyridine (0.29 ml) and methylene chloride (30 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. A second portion (0.158 ml) of methanesulphonyl chloride was added and the resultant mixture was stirred at ambient temperature for a further 18 hours. The reaction mixture was washed with water, dried (MgSO4) and evaporated. The residue was triturated under diethyl ether. The solid so obtained was dried under vacuum at 60° C. There was thus obtained the title compound (0.97 g); NMR Spectrum: (DMSOd6) 2.2 (s, 3H). 3.03 (s, 3H), 3.2 (t, 4H), 3.74 (t, 4H), 7.17 (m, 1H), 7.23 (d, 1H), 7.4 (m, 5H), 7.59 (m, 1H), 7.7 (d, 1H), 7.8 (m, 2H), 9.93 (d, 2H), 10.14 (s, 1H); Mass Spectrum: M+H+ 509.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was triturated under diethyl ether
  5. customThe solid so obtained
  6. customwas dried under vacuum at 60° C

Sources & evidence

ORD record
ord-b9f0bb8b010c4cce956315d0a75f6985
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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