Nitrogen → 6-Bromopyrrolo[2,1-F][1,2,4]triazin-4-amine

HRID 1094881

반응식

HRID 1094881 반응식
Cl.[NH2:2][N:3]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]1C#N.[C:11](O)(=O)C.[CH:15]([NH2:17])=[NH:16].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N#N>C(O)C>[Br:8][C:6]1[CH:5]=[C:4]2[N:3]([CH:7]=1)[N:2]=[CH:11][N:16]=[C:15]2[NH2:17]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 160693Formamidine acetateHCID 666412681-Amino-4-bromo-1H-pyrrole-2-carbonitrile hydrochloride

생성물 1

HCID 579552016-Bromopyrrolo[2,1-F][1,2,4]triazin-4-amine수율 75.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred suspension of 1-Ammo-4-bromo-1H-pyrrole-2-carbonitrile hydrochloride (17 g, 61.1 mmol) in absolute ethanol (350 mL) was added formamidine acetate (31.8 g, 305 mmol) and potassium phosphate (64.9 g, 305 mol). The suspension was heated for 18 hours @ 78° C. (under N2), then cooled, filtered and concentrated to dryness in vacuo. The residue was mixed with ice water (2 L) and the dark grayish-brown solids were collected by suction filtration. The solids were taken up in refluxing MeOH and treated with decolorizing carbon, then filtered thru Celite and concentrated dryness in vacuo. The solids were taken up in THF:DCE (1:3) and filtered thru a pad of silica. Removal of the solvent in vacuo provided a yellowish-brown solid. This material was recrystallized from THF:hexanes to provide the desired compound as a yellow solid (9.86 g, 75% yield). (81%). 1H-NMR (DMSO): δ 7.85 (bs, 2H), 7.81 (s, 1H), 7.80 (d, 1H, J=2 Hz), 6.96 (d, 1H, J=2 Hz).

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated to dryness in vacuo
  4. additionThe residue was mixed with ice water (2 L)
  5. filtrationthe dark grayish-brown solids were collected by suction filtration
  6. temperaturein refluxing MeOH
  7. additiontreated with decolorizing carbon
  8. filtrationfiltered thru Celite
  9. concentrationconcentrated dryness in vacuo
  10. filtrationfiltered
  11. customRemoval of the solvent in vacuo
  12. customprovided a yellowish-brown solid
  13. customThis material was recrystallized from THF

출처 및 근거

ORD 기록
ord-6a0738458c02483da5c1d03d9ad4940e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133995B2

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