6-Aminoquinoline → 2-(5-Cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-4,4,4-trifluorobutanamide

HRID 332729노트

반응식

HRID 332729 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([C:3]1[N:4]=[CH:5][C:6]([NH:8][CH:9]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)#[N:19]

참가 물질

7

반응물 4

HCID 113736-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 866855372-(6-Chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamide

생성물 1

HCID 866855382-(5-Cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-4,4,4-trifluorobutanamide수율 5.5%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 2-(6-chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamide (67 mg, 0.228 mmol), 6-aminoquinoline (48 mg, 0.333 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give 2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-4,4,4-trifluorobutanamide (5 mg).

후처리

  1. customwas degassed with Ar
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-d157cd24946a45f99c551c11a9275dd7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877760B2

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