4-[(Acetylamino)methyl]benzeneboronic acid → methyl 8-(4-(acetamidomethyl)phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

HRID 1478363Notes

Reaction equation

HRID 1478363 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].[C:21]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:23])[CH3:22]>>[C:21]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]3=[O:20])=[CH:28][CH:27]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 223094544-[(Acetylamino)methyl]benzeneboronic acidHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696756methyl 8-(4-(acetamidomethyl)phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylateYield 99.6%

Procedure

Methyl 8-(4-(acetamidomethyl)phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and (4-(acetamidomethyl)phenyl)-boronic acid (79.3 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (137 mg, 99%).

Workup

  1. customMethyl 8-(4-(acetamidomethyl)phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-29ef03e7de53497488168a8fabe3a90d
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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