4-(Trifluoromethoxy)aniline → 2-[4-(Trifluoromethoxy)phenylamino]-6-(3-acetamidophenyl)-pyrazine

HRID 16260

반응식

HRID 16260 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[F:18][C:19]([F:28])([F:29])[O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:13]2[N:12]=[C:11]([C:7]3[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=3)[CH:16]=[N:15][CH:14]=2)=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 6008484-(Trifluoromethoxy)anilineHCID 634876Binap, (A+-)-HCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

생성물 1

HCID 116396492-[4-(Trifluoromethoxy)phenylamino]-6-(3-acetamidophenyl)-pyrazine수율 20.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Using Method K, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 4-(trifluoromethoxy)aniline (51 mg, 0.29 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 80° C. for 12 hours. The same workup as for Method K and a combination of column chromatography and preparative TLC furnished 19 mg of title compound. Yield: 20.4%. 1H NMR (250 MHz, DMSO-d6) δ 2.10 (s, 3 H), 7.34-7.47 (m, 3 H), 7.60 (d, 1 H, 7.9 Hz), 7.74 (d, 1 H, 7.8 Hz), 8.00 (d, 2 H, 9.1 Hz), 8.21 (s, 1 H), 8.51 (bs, 2 H), 9.82 (s, 1 H), 10.10 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 24.09, 117.01, 119.09, 119.87, 120.94, 121.68, 129.15, 130.40, 133.52, 136.73, 139.92, 141.96, 141.99, 147.66, 151.00, 168.45; m/z 389.3 [(M+H)+, calcd for C19H15F3N4O2 388.1].

후처리

  1. customwere reacted at 80° C. for 12 hours

출처 및 근거

ORD 기록
ord-c7b0b891825b4026b01e76a3fd26e793
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737152B2

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