2-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate → (4-Fluoro-2-{1-methyl-5-[(6-methyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)amino]-6-oxo-1,6-dihydropyridin-3-yl}-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7] trideca-1(9),2(7)-dien-5-yl}phenyl)methyl Acetate
Reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[S:22][C:21]4[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=4[C:15]=3[CH2:14][CH2:13]2)=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[CH:32]=[C:31]([NH:33][C:34]2[CH:38]=C(C3CC3)N[N:35]=2)[C:30](=[O:42])[N:29]([CH3:43])[CH:28]=1)(=[O:3])[CH3:2].BrC1C=C(NC2C=[CH:62][C:61]3[CH2:60][N:59]([CH3:64])[CH2:58][CH2:57][C:56]=3N=2)C(=O)N(C)C=1.C(OCC1C(B2OC(C)(C)C(C)(C)O2)=CC=CC=1N1C(=O)C2SC3CCCCC=3C=2CC1)(=O)C>>[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[S:22][C:21]4[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=4[C:15]=3[CH2:14][CH2:13]2)=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[CH:32]=[C:31]([NH:33][C:34]2[CH:38]=[CH:62][C:61]3[CH2:60][N:59]([CH3:64])[CH2:58][CH2:57][C:56]=3[N:35]=2)[C:30](=[O:42])[N:29]([CH3:43])[CH:28]=1)(=[O:3])[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
Following the procedures as described for 136e and starting with 5-bromo-1-methyl-3-(6-methyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-ylamino)pyridine-2(1H)-one 205b and (4-fluoro-2-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate 212b, compound 223a was obtained in 50% yield.
Sources & evidence
- ORD record
- ord-06bda4888381422cb1f10a2e491c2319
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618107B2
Reaction notes
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