1,1-Dichloroethane → HCID 89923274, compound

HRID 921817Notes

Reaction equation

HRID 921817 reaction equation
C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O.ClC(Cl)C.[Cl:20][C:21]1[C:26]([NH:27][C:28]2[N:33]=[C:32]([N:34]([CH:44]3[CH2:46][CH2:45]3)CC3C=CC(OC)=CC=3)[C:31]3=[N:47][CH:48]=[C:49]([C:50]#[N:51])[N:30]3[N:29]=2)=[CH:25][C:24]([C:52]#[N:53])=[CH:23][C:22]=1[N:54]1[CH2:59][CH2:58][CH:57]2[N:60]([C:63]([O:65][CH3:66])=[O:64])[CH2:61][CH2:62][CH:56]2[CH2:55]1>>[Cl:20][C:21]1[C:26]([NH:27][C:28]2[N:33]=[C:32]([NH:34][CH:44]3[CH2:45][CH2:46]3)[C:31]3=[N:47][CH:48]=[C:49]([C:50]#[N:51])[N:30]3[N:29]=2)=[CH:25][C:24]([C:52]#[N:53])=[CH:23][C:22]=1[N:54]1[CH2:59][CH2:58][CH:57]2[N:60]([C:63]([O:65][CH3:66])=[O:64])[CH2:61][CH2:62][CH:56]2[CH2:55]1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 118253354methyl 5-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 89923274HCID 89923274, compoundYield 75.2%

Procedure

Anisole (0.027 ml, 0.244 mmol) and 25% TFA in dichloroethane (2 ml, 6.49 mmol) were added to methyl 5-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (28 mg, 0.0429 mmol) and the resulting solution was stirred at room temperature over the weekend. Solvent was evaporated in vacuo and the residue was dissolved in acetonitrile and neutralized with 2N ammonia in methanol. Desired product precipitated and was collected by filtration, methyl 5-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (17.2 mg) was obtained as a white solid.

Workup

  1. customSolvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in acetonitrile and neutralized with 2N ammonia in methanol
  3. customDesired product precipitated
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5f7e81a29d614f5b869039053fb8f4c0
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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