4-Methylmorpholine → 3-(1-Pyrrolidin-1-ylindan-5-yl)propynoic acid-(4'-chlorobiphenyl-4-yl)amide

HRID 735031

반응식

HRID 735031 반응식
[N:1]1([CH:6]2[C:14]3[C:9](=[CH:10][C:11]([C:15]#[C:16][C:17](O)=[O:18])=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC(C)C)=O.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1>C1COCC1.ClCCl>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:17](=[O:18])[C:16]#[C:15][C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][CH:12]=3)[CH:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:7][CH2:8]4)=[CH:44][CH:43]=2)=[CH:40][CH:41]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 86754-Amino-4'-chlorodiphenylHCID 62365Isobutyl chloroformateHCID 68817830(1-pyrrolidin-1-ylindan-5-yl)propynoic Acid

생성물 1

HCID 578458263-(1-Pyrrolidin-1-ylindan-5-yl)propynoic acid-(4'-chlorobiphenyl-4-yl)amide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 0.1 g (0.39 mmol) of (1-pyrrolidin-1-ylindan-5-yl)propynoic acid and 47 mL (0.43 mmol) of N-methylmorpholine in 5 mL of absolute THF is combined with 56 mL (0.43 mmol) of isobutyl chloroformate at −15° C. and stirred for ten minutes. Then 87 mg (0.43 mmol) of 4′-chlorobiphenyl-4-ylamine are added at ambient temperature and the reaction mixture is stirred for 14 hours. Then 3 mL of dichloromethane are added to the reaction mixture and this is stirred for 48 hours. Then the reaction mixture is filtered, the filtrate is evaporated down, combined with water and extracted with dichloromethane. The organic phase is evaporated down. The purification is carried out by preparative HPLC (eluant: dichloromethane/methanol/ammonia=8:2:0.2). Yield: 9 mg (5.7% of theory); C28H25ClN2O (M=440.97); calc.: molecular ion peak (M+H)+: 441/443; found: molecular ion peak (M+H)+: 441/443.

후처리

  1. stirringthe reaction mixture is stirred for 14 hours
  2. stirringthis is stirred for 48 hours
  3. filtrationThen the reaction mixture is filtered
  4. customthe filtrate is evaporated down
  5. extractionextracted with dichloromethane
  6. customThe organic phase is evaporated down
  7. customThe purification

출처 및 근거

ORD 기록
ord-64650fb27cab4cff868ecdc8f02998ed
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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