1,2-Dichloroethane → 1,3-Dihydro-5-phenyl-3(RS)-(3-trifluoromethylthiobenzoylamino)-2H-1,4-benzodiazepin-2-one

HRID 620579ノート

反応式

HRID 620579 の反応式
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](O)=[S:26].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[C:9]1([C:7]2[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3](=[O:19])[CH:2]([NH:1][C:25](=[S:26])[C:24]3[CH:28]=[CH:29][CH:30]=[C:22]([C:21]([F:20])([F:31])[F:32])[CH:23]=3)[N:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-oneHCID 178526136HCID 178526136、化合物

生成物 1

HCID 200632131,3-Dihydro-5-phenyl-3(RS)-(3-trifluoromethylthiobenzoylamino)-2H-1,4-benzodiazepin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3(RS)-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (80.0 mg, 0.318 mmole), 3-trifluoromethylthiobenzoic acid (70.7 mg, 0.318 mmole), HBT (43.0 mg, 0.318 mmole) and EDC(61.0 mg, 0.318 mmole) were combined in dry DMF (2 ml) and stirred at room temperature. The pH of the mixture was adjusted to 9.0-9.5 with triethylamine (64.4 mg, 0.636 mmole) and the mixture stirred for 10 minutes. The DMF was removed in vacuo, and the residue was treated with 10% citric acid and extracted with EtOAc. The combined organic fractions were washed with sodium carbonate solution, dried over Na2SO4, filtered, and evaporated to dryness in vacuo. The residue was crystallized from EtOAc to give the title compound which was dried in vacuo at 100° C.: (m.p. 230°-232° C.).

後処理

  1. stirringthe mixture stirred for 10 minutes
  2. customThe DMF was removed in vacuo
  3. additionthe residue was treated with 10% citric acid
  4. extractionextracted with EtOAc
  5. washThe combined organic fractions were washed with sodium carbonate solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was crystallized from EtOAc

出典と根拠

ORDレコード
ord-a84dfa094c974200a6e96025dbe3a669
出典データセット
uspto-grants-1989_04
特許番号
US04820834

反応ノート

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