HCID 118131461, compound → HCID 118131174, compound

HRID 634498Notes

Reaction equation

O[CH:2]([C:4]1[O:5][C:6](=[O:26])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[F:27][C:28]1[CH:29]=[C:30]([C:36]2[C:44]3[C:39](=[N:40][CH:41]=[N:42][C:43]=3[NH2:45])[NH:38][N:37]=2)[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1>>[NH2:45][C:43]1[N:42]=[CH:41][N:40]=[C:39]2[N:38]([CH:2]([C:4]3[O:5][C:6](=[O:26])[C:7]4[C:12]([C:13]=3[C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]5[CH2:22][CH2:23][CH2:24][CH2:25]5)=[CH:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH3:3])[N:37]=[C:36]([C:30]3[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:28]([F:27])[CH:29]=3)[C:44]=12

Participants

Reactant 2

HCID 118131461HCID 118131461, compound

HCID 178492931HCID 178492931, compound

Product 1

HCID 118131174HCID 118131174, compoundYield 26.5%

Procedure

The title compound was made in a similar way as that of the example 134, step a, from 3-(1-hydroxyethyl)-4-(4-(pyrrolidin-1-ylmethyl)phenyl)-1H-isochromen-1-one (Intermediate B47, 380 mg, 1.088 mmol) and 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G1, 310 mg, 1.197 mmol) to give 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-(pyrrolidin-1-ylmethyl)phenyl)-1H-isochromen-1-one (170 mg, 0.288 mmol, 26.5% yield) as a brown solid.

Sources & evidence

ORD record: ord-2f8e7664947c4fd1a98792d018d9fd0b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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