4-(Carbamoylamino)benzeneboronic acid, pinacol ester → methyl 1-cyclopropyl-9-methyl-4-oxo-8-(4-ureido-phenyl)-4H-quinolizine-3-carboxylate

HRID 1478340Notes

Reaction equation

HRID 1478340 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].CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH2:38])=[O:37])=[CH:31][CH:30]=2)O1>>[NH:35]([C:32]1[CH:33]=[CH:34][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:30][CH:31]=1)[C:36]([NH2:38])=[O:37]

Participants

3

Reactant 2

HCID 167274404-(Carbamoylamino)benzeneboronic acid, pinacol esterHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696566methyl 1-cyclopropyl-9-methyl-4-oxo-8-(4-ureido-phenyl)-4H-quinolizine-3-carboxylateYield 28.5%

Procedure

Methyl 8-(4-ureido-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 (75 mg, 0.26 mmol) and 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-urea (84 mg, 0.32 mmol). Compound precipitated from solution and was filtered off and dried in vacuum to afford the title compound as a yellow solid (29 mg, 26%).

Workup

  1. customMethyl 8-(4-ureido-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customCompound precipitated from solution
  3. filtrationwas filtered off
  4. customdried in vacuum

Sources & evidence

ORD record
ord-9ce93a829b1848ec82f5f3e013851007
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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