5-bromo-3-(5-(1-ethylazetidin-3-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one → (2-{4,4-Dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-6-(5-{[5-(1-ethylazetidin-3-yl)pyridin-2-yl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluorophenyl)methyl Acetate

HRID 1919061Notes

Reaction equation

HRID 1919061 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:20][N:19]([CH2:21][CH3:22])[CH2:18]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:23]([O:26][CH2:27][C:28]1[C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][C:31]([F:43])=[CH:30][C:29]=1[N:44]1[CH2:55][CH2:54][C:53]2[C:52]3[CH2:51][C:50]([CH3:57])([CH3:56])[CH2:49][C:48]=3[S:47][C:46]=2[C:45]1=[O:58])(=[O:25])[CH3:24]>>[C:23]([O:26][CH2:27][C:28]1[C:33]([C:2]2[CH:3]=[C:4]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([CH:17]4[CH2:20][N:19]([CH2:21][CH3:22])[CH2:18]4)=[CH:13][N:12]=3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:32][C:31]([F:43])=[CH:30][C:29]=1[N:44]1[CH2:55][CH2:54][C:53]2[C:52]3[CH2:51][C:50]([CH3:57])([CH3:56])[CH2:49][C:48]=3[S:47][C:46]=2[C:45]1=[O:58])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 580441415-bromo-3-(5-(1-ethylazetidin-3-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneHCID 67016224(2-{4,4-Dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl Acetate

Product 1

HCID 68208433(2-{4,4-Dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-6-(5-{[5-(1-ethylazetidin-3-yl)pyridin-2-yl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluorophenyl)methyl AcetateYield 37%

Procedure

Following Example 136a, starting with 5-bromo-3-(5-(1-ethylazetidin-3-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one 250a and (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate 247b, compound 257a was obtained in 37% yield.

Sources & evidence

ORD record
ord-bcbab38bd9bc40b4b89c7ea9abe3e668
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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