Trifluoroacetic acid → HCID 178509918, compound

HRID 1952366Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:12](=[O:50])[N:13]([CH2:21][C:22]3[C:30]4[C:25](=[N:26][C:27]([NH:31]CC5C=CC(OC)=CC=5)=[CH:28][CH:29]=4)[N:24](CC4C=CC(OC)=CC=4)[N:23]=3)[CH:14]=[CH:15][C:16]=2[C:17]([F:20])([F:19])[F:18])[CH:9]=1)[C:5]#[N:6].[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>>[F:54][C:53]([F:56])([F:55])[C:51]([O-:57])=[O:52].[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)[O:10][C:11]1[C:12](=[O:50])[N:13]([CH2:21][C:22]2[C:30]3[C:25](=[N:26][C:27]([NH3+:31])=[CH:28][CH:29]=3)[NH:24][N:23]=2)[CH:14]=[CH:15][C:16]=1[C:17]([F:18])([F:19])[F:20]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 595297293-chloro-5-{[1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

Product 1

HCID 178509918HCID 178509918, compound

Procedure

3-chloro-5-{[1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile (0.185 g, 0.264 mmol) was dissolved in TFA (5 mL) and placed in an oil bath at 75° C. After 2 hours, the reaction mixture was concentrated under reduced pressure and purified by preparative HPLC eluting with 30-95% MeCN/H2O+0.1% TFA to afford the title compound as a solid. 1H NMR (DMSO-d6, with NH4OH) δ 7.94 (d, J=7.3 Hz, 1H), 7.77-7.74 (m, 1H), 7.62-7.56 (m, 2H), 7.50-7.46 (m, 1H), 6.60 (d, J=7.3 Hz, 1H), 6.38-6.33 (m, 2H), 6.30 (d, J=8.8 Hz, 1H), 5.32 (s, 2H). HRMS (M+1)=461.0729.

Workup

customplaced in an oil bath at 75° C
concentrationthe reaction mixture was concentrated under reduced pressure
custompurified by preparative HPLC
washeluting with 30-95% MeCN/H2O+0.1% TFA

Sources & evidence

ORD record: ord-cde973c634dd45d8aef8ea5f231c4ad6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404856B2

Reaction notes

Loading…