Cesium carbonate → 4-(1-Phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamide

HRID 513273노트

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HRID 513273 반응식
Cl[C:2]1[CH:10]=[C:9]([NH:11][C:12]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13]2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:37])[CH2:35][CH3:36])[CH2:30][CH2:29]2)=[CH:24][CH:23]=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.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:15]1([C:12]2([NH:11][C:9]3[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=[C:2]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:29][CH2:30][N:31]([C:34](=[O:37])[CH2:35][CH3:36])[CH2:32][CH2:33]5)=[CH:26][CH:27]=4)[CH:10]=3)[CH2:14][CH2:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 9347841-(4-(4-Aminophenyl)piperazin-1-yl)propan-1-oneHCID 866645416-Chloro-4-(1-phenylcyclopropylamino)nicotinamide

생성물 1

HCID 569706444-(1-Phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamide수율 19%

시약·촉매·용매 2

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

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온도
80 °C

실험 절차

To a solution of 6-chloro-4-(1-phenylcyclopropylamino)nicotinamide (50 mg, 0.174 mmol) in dioxane (1 mL) was added 1-(4-(4-aminophenyl)piperazin-1-yl)propan-1-one (61 mg, 0.261 mmol), BINAP (22 mg, 0.035 mmol), Pd(OAc)2 (8 mg, 0.035 mmol) and Cs2CO3 (170 mg, 0.52 mmol). After degassed with Argon, the mixture was heated at 80° C. for 15 h. The mixture was diluted with dioxane, precipitate was filtered off, filter cake was washed with AcCN, the filtrate was concentrated and purified by preparative HPLC to give of 4-(1-phenylcyclopropylamino)-6-(4-(4-propionylpiperazin-1-yl)phenylamino)nicotinamide (16 mg). MS found for C28H32N6O2 as (M+H)+ 485.5. λ=258.2.

후처리

  1. customAfter degassed with Argon
  2. additionThe mixture was diluted with dioxane, precipitate
  3. filtrationwas filtered off
  4. filtrationfilter cake
  5. washwas washed with AcCN
  6. concentrationthe filtrate was concentrated
  7. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-cb4b8f6e590c4cc29ddb94d837a7f46b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102625B2

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