Ammonia → N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine

HRID 63364

반응식

HRID 63364 반응식
C(#N)C.[CH2:4]([C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[C:17]([CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([NH:31]C(=O)OC(C)(C)C)=[CH:23][CH:22]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[N:8][CH:7]=1)[CH3:5].S(=O)(=O)(O)O.N>O>[NH2:31][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:20][CH2:19][C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:10]3[CH:9]=[N:8][CH:7]=[C:6]([CH2:4][CH3:5])[N:11]=3)[CH:18]=2)=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 118317293Tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate2회

생성물 1

HCID 118305959N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine수율 75%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
20 °C

실험 절차

Acetonitrile (200 mL) was added to tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate (Intermediate D (protected)) (10.5 g) and the heterogeneous mixture was stirred at 20° C. Sulfuric acid (4.5 eq, 5.5 mL) was added over 2 h at 20° C. The heterogeneous mixture was stirred for an additional 2 h at 20° C. Aqueous ammonia (10 eq, 17 mL) was added to the reaction mixture over 15 min and the temperature was kept at 20° C. by cooling. Water (33.4 mL) was added to the heterogeneous mixture over 5 min at 20° C. After stirring for 30 min at 20° C., the mixture was cooled to 5° C. and stirred for an additional 2 h at 5° C. The precipitate was filtered and washed with water (33.4 mL) and 2-propanol (18 mL). The product was dried at 50° C. in vacuo for 24 h to give N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine (6.2 g, 75%).

후처리

  1. stirringThe heterogeneous mixture was stirred for an additional 2 h at 20° C
  2. customwas kept at 20° C.
  3. temperatureby cooling
  4. stirringAfter stirring for 30 min at 20° C.
  5. temperaturethe mixture was cooled to 5° C.
  6. stirringstirred for an additional 2 h at 5° C
  7. filtrationThe precipitate was filtered
  8. washwashed with water (33.4 mL) and 2-propanol (18 mL)
  9. customThe product was dried at 50° C. in vacuo for 24 h

출처 및 근거

ORD 기록
ord-1c0ec419f4984b08b49b9cfe7ad78153
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447076B2

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