Triethylamine → HCID 59505623, compound
Reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@H:10]1[C:18]2[C:13](=[CH:14][C:15]([F:23])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=2)[CH2:12][CH2:11]1.[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH:9][C@H:10]1[C:18]2[C:13](=[CH:14][C:15]([F:23])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=2)[CH2:12][CH2:11]1)=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylamine (2.5 eq.) was added to a solution of (R)-methyl 3-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylate hydrochloride (A-11) (0.773 mmol, 1 eq.) in methylene chloride (6 ml) at 0° C. and the mixture was stirred for 10 min. 2-Chlorobenzoyl chloride (1.2 eq.) was added dropwise to the reaction mixture at the same temperature and the mixture was stirred for 16 h at room temperature. The reaction mixture was diluted with methylene chloride (50 ml) and was then washed with NH4Cl solution (20 ml) and sat. NaCl solution (20 ml). The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo. The crude material was purified by column chromatography (silica gel, ethyl acetate/cyclohexane 2:1) to yield the desired product (B-15). Yield: 97%
Workup
- stirringthe mixture was stirred for 16 h at room temperature
- washwas then washed with NH4Cl solution (20 ml) and sat. NaCl solution (20 ml)
- dry with materialThe organic phase was dried over magnesium sulfate
- customthe solvent was removed in vacuo
- customThe crude material was purified by column chromatography (silica gel, ethyl acetate/cyclohexane 2:1)
Sources & evidence
- ORD record
- ord-efe87691344d4ac0af0b2dc05566b69c
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455475B2
Reaction notes
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