Dimethylcarbamoyl Chloride → HCID 44200495, compound

HRID 602289Notes

Reaction equation

HRID 602289 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH3:27])[CH:3]=1.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>C(Cl)Cl>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([C:30](=[O:31])[N:29]([CH3:33])[CH3:28])[CH2:21][CH2:22]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 59510479HCID 59510479, compound

Product 1

HCID 44200495HCID 44200495, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-amino-5-chloro-2-methoxy-N-[{4-(4-piperidinylmethyl)-2-morpholinyl}methyl]-benzamide (Example 23) (1.0 g) and a solution of TEA (0.53 ml) in methylene chloride (20 ml) was added dropwise dimethylcarbamoyl chloride (0.30 g) under ice-cooling. After completion of addition, the internal temperature of the reaction solution was warmed to room temperature, and the solution was stirred for 3 hours. The reaction solution was washed with water, then brine, and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=30/1) to give the titled compound (1.1 g) as a white solid. Melting point 179-180° C. (recrystallized from EA)

Workup

  1. temperaturecooling
  2. additionAfter completion of addition
  3. washThe reaction solution was washed with water
  4. dry with materialbrine, and then dried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-f96ddc64231d4468afb7e33893372087
Source dataset
uspto-grants-2011_03
Patent number
US07906510B2

Reaction notes

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