Phenyl chloroformate → HCID 71811136, compound

HRID 1887963Notes

Reaction equation

HRID 1887963 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:29])[C:7]([CH2:18][NH:19][C:20]([NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:34]1([O:33][C:31]([N:26]2[CH2:27][CH2:28][CH:23]([NH:22][C:20]([NH:19][CH2:18][C:7]3[C:6](=[O:29])[C:5]4[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:8]=3)=[O:21])[CH2:24][CH2:25]2)=[O:32])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 71208602HCID 71208602, compound2×

Product 1

HCID 71811136HCID 71811136, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 20 mL round-bottomed flask, 1-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methyl)-3-(piperidin-4-yl)urea (intermediate N) (0.100 g, 0.243 mmol), phenyl chloroformate (38.1 mg, 30.6 μL, 0.243 mmol) and N,N-diisopropylethylamine (157 mg, 213 μL, 1.22 mmol) were combined with CH2Cl2 (5 ml). The reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated. The crude product was purified using preparative reverse-phase HPLC to give 4-[3-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-ureido]-piperidine-1-carboxylic acid phenyl ester. MS calcd. for C29H28ClN4O4 [(M+H)+] 531.2, obsd. 531.0.

Workup

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

Sources & evidence

ORD record
ord-c6edd2a3a2924837bf8e07bdab095d73
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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