Phenyl chloroformate → HCID 71486752, compound

HRID 1887950Notes

Reaction equation

HRID 1887950 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:25]1([O:24][C:22](=[O:23])[NH:1][CH2:2][C:3]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:4]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one

Product 1

HCID 71486752HCID 71486752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one intermediate D (0.05 g, 0.176 mmol), phenyl chloroformate (27.5 mg, 0.176 mmol) and N,N-diisopropylethylamine (68.1 mg, 92.0 μL, 0.527 mmol) were combined with CH2Cl2 (3 mL). The reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, then the crude product was purified using preparative reverse-phase HPLC to provide (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-carbamic acid phenyl ester. MS calcd. for C24H18ClN5O [(M+H)+] 405.1, obsd. 404.9.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-bf73a01b940c4b45abfec0ff6d8fb367
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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