Diisopropylethylamine → HCID 71217384, compound

HRID 1887970Notes

Reaction equation

HRID 1887970 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.[N:21]1([C:27](Cl)=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12](=[O:13])[C:3]([CH2:2][NH:1][C:27]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:28])=[CH:4][N:5]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Product 1

HCID 71217384HCID 71217384, 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), morpholine-4-carbonyl chloride (26.3 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 and monitored by LC/MS. The crude product was purified using preparative reverse-phase HPLC, giving the desired product morpholine-4-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide. MS calcd. for C21H21ClN3O3 [(M+H)+] 398.1, obsd. 398.0.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-dc60a0c7bb394cc1a9cbb4b4dc05fe59
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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