Chloride 2-chloropyridinium 1-oxide → HCID 22598996、化合物

HRID 1007676

反応式

HRID 1007676 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1.Cl.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=1[O-:26].C(=O)(O)[O-].[Na+]>C(O)CCC>[OH:26][N:21]1[CH:20]=[CH:25][CH:24]=[CH:23][CH:22]1[NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1

参加物

5

反応物 3

HCID 88478Chloride 2-chloropyridinium 1-oxide2 回HCID 516892Sodium Bicarbonate2 回HCID 10585718HCID 10585718、化合物

生成物 1

HCID 22598996HCID 22598996、化合物収率 44%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

Ethyl 1-(2-aminoethyl)-1H-indazole-5-carboxylate (584 mg, 2.5 mmol, prepared as in step B), was added to dry n-butanol along with 2-chloropyridine-N-oxide hydrochloride (847 mg, 5.1 mmol) and anhydrous sodium bicarbonate (850 mg, 10.1 mmol). The reaction mixture was vigorously stirred and heated at 100C for 21 hr. Additional aliquots of 2-chloropyridine-N-oxide hydrochloride (847 mg, 5.1 mmol) and anhydrous sodium bicarbonate (850 mg, 10.1 mmol) were added and heating continued for 24 hours. The reaction was cooled and filtered and the filtrate concentrated. The residue was purified by flash chromatography (5% methanol-dichloromethane) and the product fractions concentrated to afford the product as an orange solid (358 mg, 44%). LRMS (ES): 327.1 ([M+H]+, 100%), 653.3 ([2M+H]+, 40%) 1HNMR (600.1343 MHz, CDCl3): 8.44 (s, 1H), 8.12 (s, 1H), 7.97 (d of t, 2H), 7.56 (bs, 1H), 7.45 (d, 1H), 7.06, (m, 1H), 6.45 (m, 1H), 6.35 (t, 1H), 4.68 (t, 2H), 4.37 (q, 2H), 3.90 (q, 2H), 1.39 (t, 3H).

後処理

  1. temperatureheating
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash chromatography (5% methanol-dichloromethane)
  6. concentrationthe product fractions concentrated

出典と根拠

ORDレコード
ord-1299ed5b852149f3949d335ec023ab8f
出典データセット
uspto-grants-2004_09
特許番号
US06794518B1

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