HCID 59219096, compound → HCID 86696765, compound

HRID 1478371Notes

Reaction equation

HRID 1478371 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].[OH:21][C:22]1[CH:36]=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][C:23]=1[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:27][C:26]([NH:25][CH2:24][C:23]1[CH:33]=[C:34]([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:35]=[CH:36][C:22]=1[OH:21])=[O:32])([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 59219096HCID 59219096, compoundHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696765HCID 86696765, compoundYield 100%

Procedure

Methyl 8-(3-(((tert-butoxycarbonyl)amino)methyl)-4-hydroxyphenyl)-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 (65 mg, 0.22 mmol) and tert-butyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (93.3 mg, 0.27 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (85 mg, 100%).

Workup

  1. customMethyl 8-(3-(((tert-butoxycarbonyl)amino)methyl)-4-hydroxyphenyl)-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-bcf0dd3078894512b00272b388b0f469
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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