3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formate

HRID 634506Notes

Reaction equation

HRID 634506 reaction equation
[CH:1]([OH:3])=[O:2].[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:22]([C:24]3[O:25][C:26](=[O:40])[C:27]4[C:32]([C:33]=3[C:34]3[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=3)=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:23])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:21])[CH:15]=3)[C:6]=12.O=[C:42]1[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:43]1>>[CH:1]([OH:3])=[O:2].[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:22]([C:24]3[O:25][C:26](=[O:40])[C:27]4[C:32]([C:33]=3[C:34]3[CH2:35][CH2:36][N:37]([CH:42]5[CH2:43][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:45]5)[CH2:38][CH:39]=3)=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:23])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:21])[CH:15]=3)[C:6]=12

Participants

3

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 1181311263-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formate

Product 1

HCID 118131307tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formateYield 19.3%

Procedure

Compound was prepared following the procedure described for the synthesis of Intermediate D24, from 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formate (300 mg, 0.551 mmol) and tert-butyl 3-oxoazetidine-1-carboxylate (236 mg, 1.379 mmol), to afford tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formate (74.4 mg, 0.106 mmol, 19.30% yield).

Workup

  1. customCompound was prepared

Sources & evidence

ORD record
ord-174ec06f8cc44cbc913e80cf916ce318
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…