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Potassium Carbonate → (R)-2-(6-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)butanamide

HRID 332781
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HRID 332781 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:15]#[N:16].[O:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.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]>[O:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[N:7]=[C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=2[C:15]#[N:16])=[CH:24][CH:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 162280964-(1,3,4-Oxadiazol-2-yl)anilineHCID 86685581(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide

생성물 1

HCID 86685582(R)-2-(6-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)butanamide수율 53.6%

시약·촉매·용매 2

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

실험 절차

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide (70 mg, 0.292 mmol), 4-(1,3,4-oxadiazol-2-yl)aniline (60 mg, 0.372 mmol), K2CO3 (80 mg, 0.579 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 (R)-2-(6-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)butanamide (57 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-60513c643c754a888677decb31329184
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877760B2

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