3-Fluorobenzylamine → HCID 56838045, compound
Reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[C:5](=[O:16])[N:4]([CH2:17][CH2:18][CH3:19])[C:3]=1[C:20]([OH:22])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:56][C:57]1[CH:58]=[C:59]([CH:62]=[CH:63][CH:64]=1)[CH2:60][NH2:61]>C(Cl)Cl>[F:56][C:57]1[CH:58]=[C:59]([CH:62]=[CH:63][CH:64]=1)[CH2:60][NH:61][C:20]([C:3]1[N:4]([CH2:17][CH2:18][CH3:19])[C:5](=[O:16])[C:6]2[C:11]([C:2]=1[CH3:1])=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:15])[F:14])[CH:7]=2)=[O:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 360 mg (1.1 mmol) 4-methyl-1-oxo-2-propyl-7-(trifluoromethyl)-1,2-dihydroisoquinoline-3-carboxylic acid in DCM (20 ml) was cooled to 0° C. and 870 mg (2.3 mmol) HATU and 0.8 ml (4.6 mmol) DIPEA were added. After stirring at 0° C. for 10 min, 0.2 ml (1.7 mmol) 3-fluoro-benzylamine was added and the RS was stirred at RT for 1 h. The mixture was then diluted with DCM (40 ml) and the organic layer was separated, washed with a sat. aq. NaHCO3-sol. (25 ml), a sat. aq. NH4Cl-sol. (20 ml), water (20 ml) and brine (20 ml), dried over Na2SO4 and concentrated in vacuo. The residue obtained was purified by CC (acetone/hexan 1:9) to yield 120 mg (0.3 mmol, 25%) N-(3-fluorobenzyl)-4-methyl-1-oxo-2-propyl-7-(trifluoromethyl)-1,2-dihydroisoquinoline-3-carboxamide (example 2). [M+H]+ 421.1.
Workup
- stirringthe RS was stirred at RT for 1 h
- customthe organic layer was separated
- washwashed with a sat. aq. NaHCO3-sol
- dry with material(20 ml), water (20 ml) and brine (20 ml), dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue obtained
- customwas purified by CC (acetone/hexan 1:9)
Sources & evidence
- ORD record
- ord-af270c5524224465b5bacf058a7cc302
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618129B2
Reaction notes
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