Sodium Chloride → (+/-)-7-(5-Cyclopropylaminomethyl-1,3,4-thiadiazol-2-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25075Notes

Reaction equation

HRID 25075 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([N:8]2[CH:14](C)[CH2:13][C:12]3[CH:16]=[C:17]4[O:22][CH2:21][O:20][C:18]4=[CH:19][C:11]=3[C:10]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)=[N:9]2)=[N:5][N:4]=1.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.[Cl-].[Na+]>CN(C)C=O>[CH:32]1([NH:35][CH2:2][C:3]2[S:7][C:6]([N:8]3[CH2:14][CH2:13][C:12]4[CH:16]=[C:17]5[O:22][CH2:21][O:20][C:18]5=[CH:19][C:11]=4[C:10]([C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[N:9]3)=[N:5][N:4]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 69828CyclopropylamineHCID 22565455HCID 22565455, compound

Product 1

HCID 22565489(+/-)-7-(5-Cyclopropylaminomethyl-1,3,4-thiadiazol-2-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5 ml of dimethylformamide, 0.44 g (0.96 mmol) of (±)-7-(5-chloromethyl-1,3,4-thiadiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (Example 34) and 0.37 ml (5.31 mmol) of cyclopropylamine was stirred at 70-80° C. for 1 h. Then the reaction mixture was poured into 20% sodium chloride solution and, the precipitated crude product was extracted into ethyl acetate. The solution was washed with water, dried and after evaporation yielded 0.39 g (85%) of the title compound, as solid foam.

Workup

  1. customthe precipitated crude product
  2. extractionwas extracted into ethyl acetate
  3. washThe solution was washed with water
  4. customdried
  5. customafter evaporation

Sources & evidence

ORD record
ord-8fc0158577f242dd9ae73273fed564cc
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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