prop-2-en-1-yl 7-(3,4-diaminophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate → HCID 178459713, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH2:14][C:13]=3[CH:25]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]>C(O)(=O)C>[CH3:22][O:21][C:19]([NH:15][C:14]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:10]=[CH:11][C:12]4[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH2:14][C:13]=4[CH:25]=3)=[CH:3][C:2]=2[N:1]=1)=[O:20]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Prop-2-en-1-yl 7-(3,4-diaminophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (2.7 g, 7.96 mmol) was taken into glacial acetic acid (15 mL) followed by addition of 1,3-(dimethoxycarbonyl)-2-methyl-2-thiopseudourea (1.81 g, 8.8 mmol) and the mixture was heated to 80° C. for 30 minutes then concentrated to a thick residue. The residue was treated with saturated aqueous sodium bicarbonate and the aqueous mixture basified with portionwise addition of solid sodium bicarbonate with pH 8-9. The aqueous mixture was then partitioned with hexanes then filtered. The filter cake was washed with water then hexanes and dried to give prop-2-en-1-yl 7-(2-{[(methyloxy)carbonyl]amino}-1H-benzimidazol-5-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (3.46 g, 100% yield) as a pale yellow solid.
Workup
- concentrationthen concentrated to a thick residue
- additionThe residue was treated with saturated aqueous sodium bicarbonate
- additionthe aqueous mixture basified with portionwise addition of solid sodium bicarbonate with pH 8-9
- customThe aqueous mixture was then partitioned with hexanes
- filtrationthen filtered
- washThe filter cake was washed with water
- dry with materialhexanes and dried
Sources & evidence
- ORD record
- ord-50920606182a4e4991d51e75d19c6023
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637499B2
Reaction notes
Loading…