Cevipabulin → 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine hydrochloride

HRID 28410Notes

Reaction equation

HRID 28410 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][NH:19][CH3:20])=[CH:10][C:9]=2[F:21])=[C:6]([NH:22][C@@H:23]([CH3:28])[C:24]([F:27])([F:26])[F:25])[N:5]2[N:29]=[CH:30][N:31]=[C:4]2[N:3]=1>CO.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:7]([C:8]2[C:9]([F:21])=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][NH:19][CH3:20])=[CH:12][C:13]=2[F:14])=[C:6]([NH:22][C@@H:23]([CH3:28])[C:24]([F:26])([F:27])[F:25])[N:5]2[N:29]=[CH:30][N:31]=[C:4]2[N:3]=1

Participants

4

Reactant 1

HCID 11488110Cevipabulin

Product 1

HCID 161030185-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 1 is dissolved in 10% methyl alcohol in methylene chloride (150 mL) and filtered. To the filtrate is bubbled hydrogen chloride gas. Concentration provides 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine hydrogen chloride salt as a light yellow solid (2.92 g).

Workup

  1. filtrationfiltered
  2. customTo the filtrate is bubbled hydrogen chloride gas
  3. concentrationConcentration

Sources & evidence

ORD record
ord-128f7baacd954c6eab269238e58097a1
Source dataset
uspto-grants-2008_09
Patent number
US07419982B2

Reaction notes

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