Thiourea → 4-[3-(2-Amino-thiazol-4-yl)-phenyl]-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265924Notes

Reaction equation

HRID 1265924 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.[NH2:27][C:28]([NH2:30])=[S:29]>C1COCC1.CCOC(C)=O>[NH2:30][C:28]1[S:29][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:11]3[CH2:17][C:16](=[O:18])[NH:15][C:14]4[CH:19]=[C:20]([Cl:26])[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]=4[N:12]=3)[CH:8]=[CH:9][CH:10]=2)[N:27]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 186132344-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186134994-[3-(2-Amino-thiazol-4-yl)-phenyl]-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 20.2%

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 (0.73 g) (Example 193a) and thiourea (0.13 g) in THF (10 mL) was heated to 60° C. for 15 min. 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 stirred with CH2Cl2 to give the title compound (0.14 g) as yellow solid.

Workup

  1. washwashed with sat. NaHCO3 solution and with brine
  2. customThe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-d36c659a66744f32910c26c62bb79f84
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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