Hydrochloric Acid → 4-(Amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)-methyl)benzonitrile hydrochloride

HRID 927197Notes

Reaction equation

HRID 927197 reaction equation
[ClH:1].C(OC(=O)[N:8](C1C=CC(C#N)=CC=1)[CH2:9][C:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]=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.O1[CH2:41][CH2:40]OCC1>>[ClH:1].[NH2:8][CH:9]([C:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=1)[C:41]1[CH:40]=[CH:14][C:10]([C:9]#[N:8])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 131735047tert-Butyl(4-Cyanophenyl)(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)methylcarbamate2×

Product 1

HCID 903113464-(Amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)-methyl)benzonitrile hydrochloride

Procedure

A solution of hydrogen chloride in 1,4-dioxane (4 M, 29.3 mL, 117 mmol) is added to a mixture of tert-butyl(4-cyanophenyl)(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)methylcarbamate (intermediate 12, 6.92 g, 14.7 mmol) in 1,4-dioxane (30 mL), and the mixture is stirred at room temperature for 2 h. All volatiles are removed under reduced pressure, and the residue is treated with tert-butyl methyl ether (50 mL). The precipitate is filtered, washed with tert-butyl methyl ether and dried. Yield: 6.10 g. ESI mass spectrum: [M+H]+=372; Retention time HPLC: 0.62 min (X011_S02).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. additionthe residue is treated with tert-butyl methyl ether (50 mL)
  3. filtrationThe precipitate is filtered
  4. washwashed with tert-butyl methyl ether
  5. customdried
  6. custom0.62 min (X011_S02)

Sources & evidence

ORD record
ord-944da44ad2d84166ac47b7697c23a29c
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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