Trifluoroacetic acid → HCID 72948500, compound

HRID 1430809Notes

Reaction equation

HRID 1430809 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH:15]3[CH2:18][C:17]([F:20])([F:19])[CH2:16]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:21]#[N:22])=[CH:4][C:3]=1[NH:23][C:24]1[N:29]=[C:28]([N:30]([CH:40]2[CH2:42][CH2:41]2)CC2C=CC(OC)=CC=2)[C:27]2=[N:43][CH:44]=[C:45]([C:46]#[N:47])[N:26]2[N:25]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH:15]3[CH2:16][C:17]([F:20])([F:19])[CH2:18]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:21]#[N:22])=[CH:4][C:3]=1[NH:23][C:24]1[N:29]=[C:28]([NH:30][CH:40]2[CH2:41][CH2:42]2)[C:27]2=[N:43][CH:44]=[C:45]([C:46]#[N:47])[N:26]2[N:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 867084932-((2-Chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 72948500HCID 72948500, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask charged with 2-((2-chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (34.9 mg, 0.053 mmol) in dichloromethane (530 μl) was added anisole (116 μl, 1.060 mmol), followed by the slow addition of trifluoroacetic acid (408 μl, 5.30 mmol). The reaction mixture was stirred at rt 2 d. Excess TFA was removed in vacuo. The crude residue was taken up in MeOH and free based using a Phenomenex Strata 1 g SCX column. The crude solid was purified via preparative LC/MS and provided 2-((2-chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (3.4 mg).

Workup

  1. customExcess TFA was removed in vacuo
  2. customThe crude solid was purified via preparative LC/MS

Sources & evidence

ORD record
ord-3011f02b2c99469bab9fbdb9f1e387bb
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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