Triethylamine → HCID 90310933, compound

HRID 927227Notes

Reaction equation

HRID 927227 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]=1[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1)[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[S:19]([CH2:22][CH3:23])(=[O:21])=[O:20].[C:41](N1C=CN=C1)(N1C=CN=C1)=[O:42]>C(#N)C>[O:42]=[C:41]1[N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=2)[C:25]2[CH2:26][CH2:27][C:28](=[O:29])[C:24]=2[CH:10]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[NH:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90311242HCID 90311242, compound2×

Product 1

HCID 90310933HCID 90310933, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (125 μL, 0.89 mmol) is added to a mixture of 4-(amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)methyl)-3-(ethylsulfonyl)benzonitrile hydrochloride (intermediate 20.2, 1.78 g, 3.56 mmol) and 1,1′-carbonyldiimidazole (720 mg, 4.45 mmol) in acetonitrile (20 mL), and the mixture is stirred at room temperature for 1 h. The mixture is concentrated under reduced pressure, and the residue is treated with water (20 mL). The precipitate is filtered and dried. Yield: 1.61 g. ESI mass spectrum: [M+H]+=490; Retention time HPLC: 0.56 min (X012_801).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionthe residue is treated with water (20 mL)
  3. filtrationThe precipitate is filtered
  4. customdried
  5. custom0.56 min (X012_801)

Sources & evidence

ORD record
ord-c97bca3ce24941be9aaa627ee16b003c
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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