3-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one → HCID 118131034, compound

HRID 634478Notes

Reaction equation

HRID 634478 reaction equation
NC1N=CN=C2N(CC3OC(=O)C4C(C=3C3C=CC=CC=3)=CC=CC=4)N=C(I)C=12.[F:30][C:31]1[CH:32]=[C:33]([C:39]2[C:47]3[C:42](=[N:43][CH:44]=[N:45][C:46]=3[NH2:48])[NH:41][N:40]=2)[CH:34]=[C:35]([O:37][CH3:38])[CH:36]=1.Br[CH:50]([C:52]1[O:53][C:54](=[O:80])[C:55]2[C:60]([C:61]=1[C:62]1[CH2:68][CH:67]3[N:69]([C:70]([O:72][CH2:73][C:74]4[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=4)=[O:71])[CH:64]([CH2:65][CH2:66]3)[CH:63]=1)=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH3:51]>>[NH2:48][C:46]1[N:45]=[CH:44][N:43]=[C:42]2[N:41]([CH:50]([C:52]3[O:53][C:54](=[O:80])[C:55]4[C:60]([C:61]=3[C:62]3[CH2:63][CH:64]5[N:69]([C:70]([O:72][CH2:73][C:74]6[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=6)=[O:71])[CH:67]([CH2:66][CH2:65]5)[CH:68]=3)=[CH:59][CH:58]=[CH:57][CH:56]=4)[CH3:51])[N:40]=[C:39]([C:33]3[CH:34]=[C:35]([O:37][CH3:38])[CH:36]=[C:31]([F:30])[CH:32]=3)[C:47]=12

Participants

4

Reactant 3

HCID 1181310463-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-oneHCID 118131386HCID 118131386, compoundHCID 178492931HCID 178492931, compound

Product 1

HCID 118131034HCID 118131034, compoundYield 92.1%

Procedure

Title compound was prepared following the procedure described for the synthesis of Intermediate D1, from 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G1, 52.4 mg, 0.202 mmol) and benzyl 3-(3-(1-bromoethyl)-1-oxo-1H-isochromen-4-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (Intermediate C40, 100 mg, 0.202 mmol) to give Benzyl 3-(3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (125 mg, 0.186 mmol, 92% yield) as a yellow solid.

Workup

  1. customTitle compound was prepared

Sources & evidence

ORD record
ord-f7cc228f1c5d4fc1a20c1899db544535
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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