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

HRID 620579노트

반응식

HRID 620579 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-a84dfa094c974200a6e96025dbe3a669
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820834

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