3-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one → 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)prop-2-yn-1-yl)(methyl)carbamate

HRID 634509Notes

Reaction equation

HRID 634509 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:77])[C:55]2[C:60]([C:61]=1[C:62]#[C:63][CH2:64][N:65]([CH3:76])[C:66](=[O:75])[O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=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:77])[C:55]4[C:60]([C:61]=3[C:62]#[C:63][CH2:64][N:65]([CH3:76])[C:66](=[O:75])[O:67][CH2:68][C:69]3[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=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 118150083benzyl (3-(3-(1-bromoethyl)-1-oxo-1H-isochromen-4-yl)prop-2-yn-1-yl)(methyl)carbamateHCID 178492931HCID 178492931, compound

Product 1

HCID 118150098Benzyl (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)prop-2-yn-1-yl)(methyl)carbamateYield 34.2%

Procedure

The 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, 165 mg, 0.638 mmol) and benzyl (3-(3-(1-bromoethyl)-1-oxo-1H-isochromen-4-yl)prop-2-yn-1-yl)(methyl)carbamate (Intermediate C41, 290 mg, 0.638 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)prop-2-yn-1-yl)(methyl)carbamate (138 mg, 0.218 mmol, 34.2% yield) as yellow solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-dbe1c4e558bc4c6aaba5f5705e1986c3
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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