Triethylamine → 4-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

HRID 44752

반응식

HRID 44752 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridineHCID 436087544-(Aminomethyl)oxan-4-ol

생성물 1

HCID 669191374-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol수율 93.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-chloro-3-nitro[1,5]naphthyridine (16.6 g, 79.0 mmol) in dichloromethane (250 mL) and triethylamine (14.3 mL, 102.7 mmol) was cooled to 4° C. A solution of 4-aminomethyltetrahydropyran-4-ol (11.4 g, 86.9 mmol) in dichloromethane (70 mL) was added dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at ambient temperature over the weekend and then it was concentrated under reduced pressure. The residue was stirred with water (300 mL). The resulting solid was isolated by filtration, rinsed with water, and dried in a vacuum oven at 50° C. for 4 hours to provide 22.53 g of 4-[(3-nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol.

후처리

  1. concentrationit was concentrated under reduced pressure
  2. stirringThe residue was stirred with water (300 mL)
  3. customThe resulting solid was isolated by filtration
  4. washrinsed with water
  5. customdried in a vacuum oven at 50° C. for 4 hours

출처 및 근거

ORD 기록
ord-b13aac86498640cbb8957bf3bf6a0172
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541438B2

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