3-((dimethylamino)methyl)-N-(4'-fluoro-4-nitro-[1,1'-biphenyl]-3-yl)azetidine-1-carboxamide → N-(4-amino-4'-fluoro-[1,1'-biphenyl]-3-yl)-3-((dimethylamino)methyl)azetidine-1-carboxamide
Reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:8][N:7]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:15]=[CH:16][C:17]=2[N+:18]([O-])=O)=[O:10])[CH2:6]1)[CH3:3]>CO.[Pd]>[NH2:18][C:17]1[CH:16]=[CH:15][C:14]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:13][C:12]=1[NH:11][C:9]([N:7]1[CH2:6][CH:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH2:8]1)=[O:10]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-((dimethylamino)methyl)-N-(4′-fluoro-4-nitro-[1,1′-biphenyl]-3-yl)azetidine-1-carboxamide (1.7 g, 4.57 mmol, 1.0 eq.) in methanol (100 mL) and was added 10% Pd/C (1.0 g, 0.94 mmol). The reaction mixture was stirred 2 h under a hydrogen atmosphere. The reaction was then filtered and the filtrate was concentrated under reduced pressure to give N-(4-amino-4′-fluoro-[1,1′-biphenyl]-3-yl)-3-((dimethylamino)methyl)azetidine-1-carboxamide (35 mg, 3% yield) as an off-white solid. ESI+ MS: m/z 343 ([M+H]+), 1HNMR (500 MHz, DMSO-d6): δ 7.61 (s, 1H), 7.53-7.51 (m, 2H), 7.36 (d, J=2.0 Hz, 1H), 7.21-7.15 (m, 3H), 6.76 (d, J=8.5 Hz, 1H), 4.98 (s, 2H), 3.99 (t, J=8.0 Hz, 2H), 3.58 (dd, J12=6.0 Hz, J13=8.0 Hz, 2H), 2.72-2.69 (m, 1H), 2.45-2.44 (m, 2H), 2.13 (s, 6H).
Workup
- filtrationThe reaction was then filtered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-009d932972d546529757f4e2e50b5b56
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447030B2
Reaction notes
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