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-6-oxo-5-({5-[4-(propan-2-yl)piperazin-1-yl]pyridin-2-yl}amino)-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

HRID 1919016Notes

Reaction equation

HRID 1919016 reaction equation
C(OCC1C(N2CCN3C4CCCCC=4C=C3C2=O)=CC=CC=1C1C=C(NC2C=CC([F:39])=CN=2)C(=O)N(C)C=1)(=O)C.[C:42]([O:45][CH2:46][C:47]1[C:52](B2OC(C)(C)C(C)(C)O2)=[CH:51][CH:50]=[CH:49][C:48]=1[N:62]1[C:74](=[O:75])[C:73]2[S:72][C:71]3[CH2:70][CH2:69][CH2:68][CH2:67][C:66]=3[C:65]=2[CH2:64][CH2:63]1)(=[O:44])[CH3:43].Br[C:77]1[CH:78]=[C:79]([NH:85][C:86]2[CH:91]=[CH:90][C:89]([N:92]3[CH2:97][CH2:96][N:95]([CH:98]([CH3:100])[CH3:99])[CH2:94][CH2:93]3)=[CH:88][N:87]=2)[C:80](=[O:84])[N:81]([CH3:83])[CH:82]=1>>[C:42]([O:45][CH2:46][C:47]1[C:48]([N:62]2[C:74](=[O:75])[C:73]3[S:72][C:71]4[CH2:70][CH2:69][CH2:68][CH2:67][C:66]=4[C:65]=3[CH2:64][CH2:63]2)=[CH:49][C:50]([F:39])=[CH:51][C:52]=1[C:77]1[CH:78]=[C:79]([NH:85][C:86]2[CH:91]=[CH:90][C:89]([N:92]3[CH2:97][CH2:96][N:95]([CH:98]([CH3:100])[CH3:99])[CH2:94][CH2:93]3)=[CH:88][N:87]=2)[C:80](=[O:84])[N:81]([CH3:83])[CH:82]=1)(=[O:44])[CH3:43]

Participants

4

Reactant 3

HCID 580437182-(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 AcetateHCID 580437585-Bromo-3-(5-(4-isopropylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneHCID 680965952-(5-(5-Fluoropyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl Acetate

Product 1

HCID 67016294{4-Fluoro-2-[1-methyl-6-oxo-5-({5-[4-(propan-2-yl)piperazin-1-yl]pyridin-2-yl}amino)-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

Procedure

Following the procedures as described for 148b and starting with 400 mg of (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 and 340 mg 5-bromo-3-(5-(4-isopropylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one 220a, compound 220b was obtained as a yellow solid (446 mg, 82%).MS: [M+H]+ 699

Sources & evidence

ORD record
ord-dd7fa3b5639349b495431bfe39d45d0f
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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