4-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one → HCID 178482571, compound

HRID 1265926Notes

Reaction equation

HRID 1265926 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH2:17][C:16](=[O:18])[NH:15][C:14]3[CH:19]=[C:20]([Cl:26])[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]=3[N:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.[C:27]([NH:30][C:31]([NH2:33])=[S:32])(=[NH:29])[NH2:28]>C1COCC1.CCOC(C)=O>[Cl:26][C:20]1[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]2[N:12]=[C:11]([C:7]3[CH:6]=[C:5]([C:3]4[N:33]=[C:31]([NH:30][C:27]([NH2:29])=[NH:28])[S:32][CH:2]=4)[CH:10]=[CH:9][CH:8]=3)[CH2:17][C:16](=[O:18])[NH:15][C:14]=2[CH:19]=1

Participants

5

Reactant 2

HCID 186132344-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-oneHCID 178513045HCID 178513045, compound

Product 1

HCID 178482571HCID 178482571, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(3-bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (130 mg) (Example 193a) and N-amidino-thiourea (35 mg) in THF (3 mL) was heated at 60° C. for 1 h. The mixture was diluted with AcOEt and washed with sat. NaHCO3 solution and with brine. The organic layer was dried and evaporated and the residue was purified by chromatography on silica gel using AcOEt/MeOH (20:1) as eluent. The purified product was crystallyzed from acetone to give the title compound (22 mg) as yellow solid.

Workup

  1. washwashed with sat. NaHCO3 solution and with brine
  2. customThe organic layer was dried
  3. customevaporated
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-022e5b594dc14187b510c67c2c081c9d
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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