8-Bromo-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1'-cyclopropane] → 1-Methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1'-cyclopropane]
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:13]3[C:14]([CH3:17])=[N:15][N:16]=[C:12]3[C:9]3([CH2:11][CH2:10]3)[CH2:8][NH:7][C:6]=2[CH:18]=1>[Pd].CO>[CH3:17][C:14]1[N:13]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:18][C:6]=3[NH:7][CH2:8][C:9]3([CH2:10][CH2:11]3)[C:12]2=[N:16][N:15]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 8-bromo-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane] (150 mg, 0.49 mmol) and palladium on carbon (40 mg) in methanol (10 mL) was stirred for 2 hours at 40° C. under hydrogen atmosphere. The solid was filtered and the filtrate was concentrated to give crude 1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane] (100 mg, 91%) as yellow oil, used for the next step without further purification. LRMS (M+H+)+: calcd 226.12. found 226.
Workup
- filtrationThe solid was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-a343e8254d5645eeb1e36633a9f12360
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422292B2
Reaction notes
Loading…