2-(Acetoxymethyl)-3-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)phenylboronic Acid Pinacol Ester → (25)-(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo-[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluoro-6-[1-methyl-5-({5-[2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]phenyl)-methyl acetate

HRID 1843147Notes

Reaction equation

HRID 1843147 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24]CC3N4C(CCCC4)=CC=3[C:13]2=[O:25])=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[CH:32]=[C:31]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][N:43]([CH:46]4[CH2:49][O:48][CH2:47]4)[CH2:42][C@@H:41]3[CH3:50])=[CH:36][N:35]=2)[C:30](=[O:51])[N:29]([CH3:52])[CH:28]=1)(=[O:3])[CH3:2].C(OCC1C(B2OC(C)(C)C(C)(C)O2)=CC=CC=1N1C[CH2:83][N:82]2[C:75](=[CH:76][C:77]3[CH2:78][C:79]([CH3:86])([CH3:85])[CH2:80][C:81]=32)C1=O)(=O)C.BrC1C=C(NC2C=CC(N3CCN(C4COC4)C[C@@H]3C)=CN=2)C(=O)N(C)C=1>>[C:1]([O:4][CH2:5][C:6]1[C:7]([C:27]2[CH:32]=[C:31]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([N:40]4[CH2:45][CH2:44][N:43]([CH:46]5[CH2:47][O:48][CH2:49]5)[CH2:42][C@@H:41]4[CH3:50])=[CH:36][N:35]=3)[C:30](=[O:51])[N:29]([CH3:52])[CH:28]=2)=[CH:8][C:9]([F:26])=[CH:10][C:11]=1[N:12]1[CH2:24][CH2:83][N:82]2[C:75](=[CH:76][C:77]3[CH2:78][C:79]([CH3:86])([CH3:85])[CH2:80][C:81]=32)[C:13]1=[O:25])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 670162762-(Acetoxymethyl)-3-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)phenylboronic Acid Pinacol EsterHCID 86683699(S)-4-Fluoro-2-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)benzyl acetateHCID 866843475-bromo-1-methyl-3-[[5-[(2S)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]pyridin-2-one

Product 1

HCID 86762454(25)-(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo-[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluoro-6-[1-methyl-5-({5-[2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]phenyl)-methyl acetateYield 24%

Procedure

Following the procedures as described for compound 101i, reaction of (2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate (229 mg, 0.46 mmol) and (S)-5-bromo-1-methyl-3-(5-(2-methyl-4-(oxetan-3-yl)piperazine-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one (200 mg, 0.46 mmol), afforded 103h as a yellow solid (80 mg, 24%). MS: [M+H]+ 724.

Sources & evidence

ORD record
ord-2ad7175186564229912e077667fa1e50
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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