Dimethylformamide → HCID 11999427, compound

HRID 1668406Notes

Reaction equation

HRID 1668406 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][NH:29][CH3:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.BrC[C:33]([NH2:35])=[O:34].[CH2:36](N(CC)CC)C.CN(C)C=O>C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:28][N:29]([CH3:36])[CH2:30][C:33]([NH2:35])=[O:34])=[CH:26][CH:27]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 696322-BromoacetamideHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Product 1

HCID 11999427HCID 11999427, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound (100 mg) obtained in Example 4, bromoacetamide (31 mg), triethylamine (73 mg) and N,N-dimethylformamide (2 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)] and recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (28 mg) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)]
  5. customrecrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-03e49a6cfbe44a82abed7db6af84bf93
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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