Binap, (A+-)- → 2-(4-tert-Butylthiazol-2-ylamino)-6-(3-acetamidophenyl)pyrazine

HRID 16265노트

반응식

HRID 16265 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].[C:18]([C:22]1[N:23]=[C:24]([NH2:27])[S:25][CH:26]=1)([CH3:21])([CH3:20])[CH3:19].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>[C:18]([C:22]1[N:23]=[C:24]([NH:27][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)[S:25][CH:26]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 4

HCID 634876Binap, (A+-)-HCID 27342024-tert-Butyl-1,3-thiazol-2-amineHCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

생성물 1

HCID 114943702-(4-tert-Butylthiazol-2-ylamino)-6-(3-acetamidophenyl)pyrazine수율 21%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Following Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 4-(tert-butyl)-1,3-thiazol-2-amine (54.7 mg, 0.35 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 85° C. for 16 hours. The same workup as is Method L produced a solid that was washed with 50 mL dichloromethane and filtered. The dichloromethane slowly evaporated to produce white crystals that were removed by filtration and washing with dichloromethane (10 mL). The dichloromethane was then evaporated and the resulting crude was chromatographed in silica gel using ethyl acetate: dichloromethane, 2:1, as eluent to furnish 18.5 mg of title compound. Yield: 21.0%. 1 H NMR (250 MHz, DMSO-d6) δ 1.30 (s, 9H), 2.10 (s, 3 H), 6.69 (s, 1 H), 7.47 (t, 1 H, 7.9 Hz), 7.69 (d, 1 H, 8.0 Hz), 7.89 (d, 1 H, 7.8 Hz), 8.38 (s, 1 H), 8.45 (bs, 1 H), 8.58 (s, 1 H), 10.11 (s, 1 H), 11.78 (bs, 1 H);

후처리

  1. customwere reacted at 85° C. for 16 hours
  2. customproduced a solid
  3. washthat was washed with 50 mL dichloromethane
  4. filtrationfiltered
  5. customThe dichloromethane slowly evaporated
  6. customto produce white crystals that
  7. customwere removed by filtration
  8. washwashing with dichloromethane (10 mL)
  9. customThe dichloromethane was then evaporated
  10. customthe resulting crude was chromatographed in silica gel

출처 및 근거

ORD 기록
ord-6f12db6018d14117a4997409e78fe5d6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737152B2

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