Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate → HCID 86696766, compound

HRID 1478372Notes

Reaction equation

HRID 1478372 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:30]=[CH:31][C:32]3[S:36][C:35]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[N:34][C:33]=3[CH:45]=2)O1>>[NH2:37][C:35]1[S:36][C:32]2[CH:31]=[CH:30][C:29]([C:2]3[CH:3]=[CH:4][N:5]4[C:10]([C:11]=3[CH3:12])=[C:9]([CH:13]3[CH2:15][CH2:14]3)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]4=[O:20])=[CH:45][C:33]=2[N:34]=1.[C:40]([O:39][C:38]([NH:37][C:35]1[S:36][C:32]2[CH:31]=[CH:30][C:29]([C:2]3[CH:3]=[CH:4][N:5]4[C:10]([C:11]=3[CH3:12])=[C:9]([CH:13]3[CH2:15][CH2:14]3)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]4=[O:20])=[CH:45][C:33]=2[N:34]=1)=[O:44])([CH3:43])([CH3:41])[CH3:42]

Participants

4

Reactant 2

HCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylateHCID 86696768HCID 86696768, compound

Product 2

HCID 86696766HCID 86696766, compoundYield 38%HCID 86696767HCID 86696767, compoundYield 20%

Procedure

The title compounds were 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 a mixture of tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate and di-tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl-di-carbamate (195.7 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded methyl 8-(2-aminobenzo[d]thiazol-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (58 mg, 38%) and yellow solid methyl 8-(2-(tert-butoxycarbonylamino)benzo[d]thiazol-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (42 mg, 20%).

Workup

  1. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-f285a4286ae74226906597862355b291
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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