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

HRID 927213ノート

反応式

HRID 927213 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-45109886c98f4cb6a52ac817e6e801bd
出典データセット
uspto-grants-2016_03
特許番号
US09290459B1

反応ノート

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