Sodium Carbonate → HCID 66678170、化合物

HRID 217777

反応式

HRID 217777 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[NH2:32][C:33]1[C:34]([C:40]([NH:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[O:41])=[N:35][C:36](Br)=[CH:37][N:38]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:32][C:33]1[N:38]=[CH:37][C:36]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][CH2:14][N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[CH:22][CH:21]=2)=[N:35][C:34]=1[C:40](=[O:41])[NH:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 104021623-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamideHCID 58065590HCID 58065590、化合物

生成物 1

HCID 66678170HCID 66678170、化合物

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the product of step (iv) (250 g, 0.58 mol), 3-amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide (220 g, 0.75 mol), Na2CO3 (183 g, 1.73 mol) and Pd(dppf)Cl2 (25.30 g, 35 mmol) in DMF (3 L) was stirred and degassed with N2 three times. The mixture was stirred at 70˜80° C. under N2 for 24 hours. The mixture was filtered and the filtrate concentrated to in vacuo to remove DMF. EtOAc (1.5 L) and H2O (800 mL) were charged and stirred for 1 hour at 10-25° C. The suspension was filtered, the organic phase was concentrated in vacuo and purified by column chromatography (PE: EtOAc=3:1-1:3). The crude product was re-crystallized from EtOAc-MeOH and filtered, the yellow solid was washed by EtOA and dried under reduced pressure. The subtitle compound (v) was obtained (pale yellow solid, 160 g).

後処理

  1. customdegassed with N2 three times
  2. stirringThe mixture was stirred at 70˜80° C. under N2 for 24 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated to in vacuo
  5. customto remove DMF
  6. additionEtOAc (1.5 L) and H2O (800 mL) were charged
  7. stirringstirred for 1 hour at 10-25° C
  8. filtrationThe suspension was filtered
  9. concentrationthe organic phase was concentrated in vacuo
  10. custompurified by column chromatography (PE: EtOAc=3:1-1:3)
  11. customThe crude product was re-crystallized from EtOAc-MeOH
  12. filtrationfiltered
  13. washthe yellow solid was washed by EtOA
  14. customdried under reduced pressure

出典と根拠

ORDレコード
ord-944616c7422747fdad1ab242d2595849
出典データセット
uspto-grants-2012_06
特許番号
US08198285B2

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