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Trifluoroacetic acid → HCID 86708565, compound

HRID 921693
Notes
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Reaction equation

HRID 921693 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:14][CH:13]([F:15])[CH2:12][N:11]([CH:16]3[CH2:19][O:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:20]#[N:21])=[CH:4][C:3]=1[NH:22][C:23]1[N:28]=[C:27]([N:29]([CH:39]2[CH2:41][CH2:40]2)CC2C=CC(OC)=CC=2)[C:26]2=[N:42][CH:43]=[C:44]([C:45]#[N:46])[N:25]2[N:24]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:14][CH:13]([F:15])[CH2:12][N:11]([CH:16]3[CH2:19][O:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:20]#[N:21])=[CH:4][C:3]=1[NH:22][C:23]1[N:28]=[C:27]([NH:29][CH:39]2[CH2:40][CH2:41]2)[C:26]2=[N:42][CH:43]=[C:44]([C:45]#[N:46])[N:25]2[N:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 86708566(+/-)2-((2-Chloro-5-cyano-3-(6-fluoro-4-(oxetan-3-yl)-1,4-diazepan-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 86708565HCID 86708565, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

(+/−)2-((2-chloro-5-cyano-3-(6-fluoro-4-(oxetan-3-yl)-1,4-diazepan-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (89 mg, 0.138 mmol) was taken up in DCE (1 mL) and anisole (0.076 mL, 0.692 mmol) was added, followed by TFA (0.640 mL, 8.30 mmol). The reaction was stirred at room temperature overnight. An additional 1 ml of TFA was added, and the reaction was stirred at room temperature for 4 h. The solvent was removed in vacuo and the material dissolved in MeOH. The material was loaded onto an SCX column (5 g, benzenesulfonic acid sorbent) and the column was flushed with MeOH, then 1:1 DCM/7N NH3/MeOH to obtain the product. The solvent was removed in vacuo and the crude material was purified by preparative HPLC. 2-((2-chloro-5-cyano-3-(6-fluoro-4-(oxetan-3-yl)-1,4-diazepan-1-yl)phenyl)amino)-4-(cyclopropyl amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (12 mg) was obtained as a yellow solid.

Workup

  1. stirringthe reaction was stirred at room temperature for 4 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe material dissolved in MeOH
  4. customthe column was flushed with MeOH
  5. custom1:1 DCM/7N NH3/MeOH to obtain the product
  6. customThe solvent was removed in vacuo
  7. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-5823a971d6264b22bfb51d783995b73e
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273057B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes