Potassium Carbonate → (R)-2-(5-cyano-6-(4-(pyridin-3-yl)phenylamino)pyrazin-2-ylamino)butanamide

HRID 332787

反応式

HRID 332787 の反応式
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].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH:18]=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]>[C:15]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:27][C:26]1[CH:25]=[CH:24][C:23]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:29][CH:28]=1)#[N:16]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 4595224-(Pyridin-3-yl)anilineHCID 634876Binap, (A+-)-HCID 86685581(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide

生成物 1

HCID 86685585(R)-2-(5-cyano-6-(4-(pyridin-3-yl)phenylamino)pyrazin-2-ylamino)butanamide収率 57.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide (100 mg, 0.417 mmol), 4-(pyridin-3-yl)aniline (77 mg, 0.452 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (3 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-(5-cyano-6-(4-(pyridin-3-yl)phenylamino)pyrazin-2-ylamino)butanamide (90 mg).

後処理

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

出典と根拠

ORDレコード
ord-7f8633bf2a204d9abc95189d4f933d76
出典データセット
uspto-grants-2014_11
特許番号
US08877760B2

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