(4-Fluoro-2-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-5-yl}-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate → {4-Fluoro-2-[1-methyl-5-({5-[(2R)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxopyridin-3-yl]-6-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-5-yl}phenyl}methyl Acetate

HRID 519356Notes

Reaction equation

HRID 519356 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][O:25][CH2:24]4)[CH2:19][C@H:18]3[CH3:27])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:28]([O:31][CH2:32][C:33]1[C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][C:36]([F:48])=[CH:35][C:34]=1[N:49]1[C:61](=[O:62])[C:60]2[S:59][C:58]3[CH2:57][CH2:56][CH2:55][CH2:54][C:53]=3[C:52]=2[CH:51]=[N:50]1)(=[O:30])[CH3:29]>>[C:28]([O:31][CH2:32][C:33]1[C:34]([N:49]2[C:61](=[O:62])[C:60]3[S:59][C:58]4[CH2:57][CH2:56][CH2:55][CH2:54][C:53]=4[C:52]=3[CH:51]=[N:50]2)=[CH:35][C:36]([F:48])=[CH:37][C:38]=1[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][O:25][CH2:24]4)[CH2:19][C@H:18]3[CH3:27])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1)(=[O:30])[CH3:29]

Participants

3

Reactant 2

HCID 58043634(4-Fluoro-2-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-5-yl}-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetateHCID 866837445-bromo-1-methyl-3-[[5-[(2R)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]-2-pyridyl]amino]pyridin-2-one

Product 1

HCID 86683746{4-Fluoro-2-[1-methyl-5-({5-[(2R)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxopyridin-3-yl]-6-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-5-yl}phenyl}methyl AcetateYield 48%

Procedure

Following the procedure in Example 102 and starting with (R)-5-bromo-1-methyl-3-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one 115f (217 mg, 0.50 mmol) and 117e (249 mg, 0.50 mmol) afforded 117f as a yellow solid (174 mg, 48%). MS: [M+H]+ 726.

Sources & evidence

ORD record
ord-ae071dc5591944a3b315a4dd8a8d5f96
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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