Trifluoroacetic acid → 4-(1-Phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide

HRID 513285

反応式

HRID 513285 の反応式
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:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=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+].C(O)(C(F)(F)F)=O>O1CCOCC1.C(Cl)Cl.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:27]=[CH:26][CH:25]=[C:24]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH:23]=4)[CH:10]=3)[CH2:14][CH2:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

9

反応物 5

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 22330182tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylateHCID 866645416-Chloro-4-(1-phenylcyclopropylamino)nicotinamide

生成物 1

HCID 569687044-(1-Phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 6-chloro-4-(1-phenylcyclopropylamino)nicotinamide (150 mg, 0.522 mmol) in p-Dioxane (4.5 mL) was added tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate (174 mg, 0.626 mmol), Pd(OAc)2 (23 mg, 0.104 mmol), BINAP (65 mg, 0.104 mmol) and Cs2CO3 (510 mg, 1.566 mmol). After stirred at 80° C. for 15 h, it was concentrated to give crude residue, which was then treated with TFA in DCM, 30 min later, the solution was concentrated, the residue was purified by preparative HPLC to give 4-(1-phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide. MS found for C25H28N6O as (M+H)+ 429.4. UV: λ=254.6 nm. 1H NMR: (CD3OD) δ 8.17 (s, 1H), 7.31-7.20 (m, 4H), 7.13 (m, 2H), 6.95 (dd, J=8.0, 2.0 Hz, 1H), 6.79 (t, J=2.0 Hz, 1H), 6.60 (dd, J=7.2, 2.0 Hz, 1H), 6.12 (s, 1H), 3.34 (m, 8H), 1.36 (m, 4H) ppm.

後処理

  1. concentrationit was concentrated
  2. customto give crude residue, which
  3. concentrationthe solution was concentrated
  4. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-1a1cca8c149e4bdda16d8f9adfe98a25
出典データセット
uspto-grants-2015_08
特許番号
US09102625B2

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