Potassium Phosphate, Tribasic → HCID 66678170, 화합물

HRID 217786

반응식

HRID 217786 반응식
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH3:18][O:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][CH:35]=1)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:37]2[CH:38]=[CH:39][C:34]([CH2:33][CH2:32][CH2:31][N:23]([CH2:22][CH2:21][CH2:20][O:19][CH3:18])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[CH:35][CH:36]=2)=[N:4][C:3]=1[C:9](=[O:10])[NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 104021623-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamideHCID 58065590HCID 58065590, 화합물

생성물 1

HCID 66678170HCID 66678170, 화합물

시약·촉매·용매 2

HCID 178479786HCID 178479786, 화합물촉매HCID 962Water용매3회

반응 조건

온도
21 °C

실험 절차

To a reactor was charged, 3-Amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide (1580 g), tert-butyl (3-methoxypropyl){3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl}carbamate (2778 g) 1-butanol (23.7 L), potassium phosphate, tribasic, N-hydrate (2740 g) and water (1.58 L). The contents were stirred under nitrogen at ambient (21° C.). In a second reactor was made up a solution of 3-(di-tert-butylphosphonium)propane sulphonate (DTBPPS) (83.04 g); sodium tetrachloropalladate (45.52 g) and water (1.58 L). The catalyst/ligand solution was poured into the reaction; the reaction was inerted and heated up to 80° C. The reaction was stirred for 2 hours at 80° C. The batch was cooled to 60° C. and water (22.1 L) was added. The contents washed with water at 60° C. The organic layer and interface were filtered through perlite (500 g) made up with 1-Butanol (3.95 L). The organic liquors were recharged to the vessel and washed with water (11.1 L) at 60° C. The organic liquor was washed with 10% w/v aqueous sodium chloride (11.2 L) at 60° C. The organic liquors were heated up to 60° C. and distilled under vacuum to ˜10 relative volumes. The batch was cooled to 20° C. and left to stir for 16 hours under nitrogen. The contents were filtered and washed with 1-Butanol (4 L×2). The yellow free flowing solid was discharged and dried in vacuum oven at 40° C. overnight (tert-butyl (3-{4-[5-amino-6-(pyridin-3-ylcarbamoyl)pyrazin-2-yl]phenyl}propyl)(3-methoxypropyl)carbamate (2428 g)).

후처리

  1. additionTo a reactor was charged
  2. customIn a second reactor was made up
  3. additionThe catalyst/ligand solution was poured into the reaction
  4. temperatureheated up to 80° C
  5. stirringThe reaction was stirred for 2 hours at 80° C
  6. temperatureThe batch was cooled to 60° C.
  7. washThe contents washed with water at 60° C
  8. filtrationThe organic layer and interface were filtered through perlite (500 g)
  9. washwashed with water (11.1 L) at 60° C
  10. washThe organic liquor was washed with 10% w/v aqueous sodium chloride (11.2 L) at 60° C
  11. temperatureThe organic liquors were heated up to 60° C.
  12. distillationdistilled under vacuum to ˜10 relative volumes
  13. temperatureThe batch was cooled to 20° C.
  14. waitleft
  15. stirringto stir for 16 hours under nitrogen
  16. filtrationThe contents were filtered
  17. washwashed with 1-Butanol (4 L×2)
  18. dry with materialdried in vacuum oven at 40° C. overnight (tert-butyl (3-{4-[5-amino-6-(pyridin-3-ylcarbamoyl)pyrazin-2-yl]phenyl}propyl)(3-methoxypropyl)carbamate (2428 g))

출처 및 근거

ORD 기록
ord-21d80952fdf84f19bc880eff7a024975
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198285B2

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