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

HRID 73687

反応式

HRID 73687 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred suspension of 1-Amino-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).

後処理

  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

出典と根拠

ORDレコード
ord-b855cc33a47c4702bcdf8e99551d67bd
出典データセット
uspto-grants-2014_09
特許番号
US08829185B2

関連ノート

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