Chloride 2-chloropyridinium 1-oxide → HCID 22598996, 화합물

HRID 1007676

반응식

HRID 1007676 반응식
[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

참가 물질

5

반응물 3

HCID 88478Chloride 2-chloropyridinium 1-oxide2회HCID 516892Sodium Bicarbonate2회HCID 10585718HCID 10585718, 화합물

생성물 1

HCID 22598996HCID 22598996, 화합물수율 44%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1299ed5b852149f3949d335ec023ab8f
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794518B1

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