Hydrochloric Acid → 4-{Amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-methylsulfanyl-benzonitrile hydrochloride

HRID 59644Notes

Reaction equation

HRID 59644 reaction equation
[ClH:1].O1CCOCC1.C(OC(=O)[NH:14][CH:15]([C:34]1[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][C:35]=1[S:42][CH3:43])[C:16]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:17]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)(C)(C)C>C(#N)C>[ClH:1].[NH2:14][CH:15]([C:16]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:17]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=1)[C:34]1[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][C:35]=1[S:42][CH3:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118692901{(4-Cyano-2-methylsulfanyl-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 1186928904-{Amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-methylsulfanyl-benzonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of hydrogen chloride in 1,4-dioxane (4 M, 4.5 mL, 18 mmol) is added to a mixture of {(4-cyano-2-methylsulfanyl-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester (INTERMEDIATE 4, 2.16 g, 3.25 mmol) in acetonitrile (4.5 mL) and the mixture is stirred at room temperature for 1 h. The precipitate is filtered off, washed with acetonitrile and dried. Yield: 1.19 g. ESI mass spectrum: [M+H-NH3]+=415; Retention time HPLC: 0.88 min (Z018_S04).

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with acetonitrile
  3. customdried
  4. custom0.88 min (Z018_S04)

Sources & evidence

ORD record
ord-a45e5ae647e149fa90c6db25ec98a17d
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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