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

HRID 927213노트

반응식

HRID 927213 반응식
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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 903113464-(Amino(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)-methyl)benzonitrile hydrochloride2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-45109886c98f4cb6a52ac817e6e801bd
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290459B1

반응 노트

불러오는 중…