Hydrochloric Acid → HCID 118692142, compound

HRID 59653Notes

Reaction equation

HRID 59653 reaction equation
C(OC(=O)[NH:7][CH:8]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][C:28]=1[Br:35])[C:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)(C)(C)C.[ClH:37].O1CCOCC1>C(#N)C>[ClH:37].[NH2:7][CH:8]([C:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1)[C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][C:28]=1[Br:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118692170{(2-Bromo-4-cyano-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 118692142HCID 118692142, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

{(2-Bromo-4-cyano-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester (INTERMEDIATE 20, 20.8 g, 36.9 mmol) is suspended in acetonitrile (150 mL) and a solution of hydrogen chloride in 1,4-dioxane (4 M, 46.1 mL, 184.3 mmol) is added. The mixture is stirred at room temperature for 3 h. The product precipitates from the reaction mixture. The precipitate is filtered off, washed with acetonitrile and dried. Yield: 16.5 g ESI mass spectrum: [M+H]+=464 (bromine isotope pattern), Retention time HPLC: 0.56 min, (X012_S02).

Workup

  1. customThe product precipitates from the reaction mixture
  2. filtrationThe precipitate is filtered off
  3. washwashed with acetonitrile
  4. customdried
  5. custom0.56 min, (X012_S02)

Sources & evidence

ORD record
ord-a203165f87654454b3c9f7ab6960ecb7
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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