N,N-Dimethylglycine → 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1-(2-(dimethylamino)acetyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formate

HRID 634410Notes

Reaction equation

HRID 634410 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:13]([C:15]3[O:16][C:17](=[O:31])[C:18]4[C:23]([C:24]=3[C:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH3:14])[N:10]=[C:11]([I:12])[C:4]=12.[CH3:32][N:33]([CH3:38])[CH2:34][C:35](O)=[O:36]>>[CH:17]([OH:31])=[O:16].[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:13]([C:15]3[O:16][C:17](=[O:31])[C:18]4[C:23]([C:24]=3[C:25]3[CH2:26][CH2:27][N:28]([C:35](=[O:36])[CH2:34][N:33]([CH3:38])[CH3:32])[CH2:29][CH:30]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH3:14])[N:10]=[C:11]([I:12])[C:4]=12

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 1181311443-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride

Product 1

HCID 1181312403-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1-(2-(dimethylamino)acetyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formateYield 108.5%

Procedure

Title compound was prepared following the procedure used for the synthesis of Intermediate D25, from 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride (Intermediate Intermediate D23, 0.200 g, 0.363 mmol) and 2-(dimethylamino)acetic acid (0.045 g, 0.436 mmol) to give the title compound (0.127 g, 0.197 mmol, 54.2% yield) as a white powder.

Workup

  1. customTitle compound was prepared

Sources & evidence

ORD record
ord-ae57654d745342a8aa370641e5519138
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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