Triethylamine → 4-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile

HRID 927213Notes

Reaction equation

HRID 927213 reaction equation
Cl.[NH2:2][CH:3]([C:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30].C(N(CC)CC)C>C(#N)C>[O:30]=[C:29]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:13]2[CH2:14][CH2:15][C:16](=[O:17])[C:12]=2[CH:3]([C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=2)[NH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 903113464-(Amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)-methyl)benzonitrile hydrochloride2×

Product 1

HCID 778447734-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)-methyl)benzonitrile hydrochloride (intermediate 13, 11.8 g, 26.1 mmol based on 90% purity) in acetonitrile (100 mL) and 1,1′-carbonyldiimidazole (5.28 g, 32.6 mmol) is treated with triethylamine (0.9 mL, 6.5 mmol), and the mixture is stirred at room temperature for 1 h. All volatiles are removed under reduced pressure, and the residue is treated with water. The precipitate is filtered, washed with water and dried. The residue is purified by recrystallization from hot toluene (130 mL). Yield: 8.6 g; ESI mass spectrum [M+H]+=398; Retention time HPLC: 1.06 min (V011_S01). LH4BRM00213

Workup

  1. customAll volatiles are removed under reduced pressure
  2. additionthe residue is treated with water
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customdried
  6. customThe residue is purified by recrystallization from hot toluene (130 mL)
  7. custom1.06 min (V011_S01)

Sources & evidence

ORD record
ord-45109886c98f4cb6a52ac817e6e801bd
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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