Potassium Carbonate → (R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide

HRID 84808

반응식

HRID 84808 반응식
Br[C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH3:15])[C:12]([NH2:14])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[NH2:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[CH:19]=1.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.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:10][C@H:11]([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:3][C:2]=1[NH:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[CH:19]=1)#[N:9]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 67509792(R)-2-(3-bromo-4-cyanophenylamino)propanamide

생성물 1

HCID 67510271(R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide수율 61.1%

시약·촉매·용매 2

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

실험 절차

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)propanamide (185 mg, 0.690 mmol), 5-amino-3-methylisothiazole hydrochloride (133 mg, 0.883 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (30 mg, 0.13 mmol) and K2CO3 (300 mg, 2.17 mmol) in dioxane (4 mL) was degassed with Ar, then was stirred at 120 C for 18 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give ((R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (127 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-be031f87a34e4e09b1fdd43daa5aadf5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846928B2

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