1,1,1-Trimethoxybutane → 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 44754노트

반응식

HRID 44754 반응식
CO[C:3](OC)(OC)[CH2:4][CH2:5][CH3:6].[NH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:19][CH:18]=[CH:17][CH:16]=2>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:4]([C:3]1[N:22]([CH2:23][C:24]2([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:21]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=1)[CH2:5][CH3:6]

참가 물질

5

반응물 2

HCID 1235121,1,1-TrimethoxybutaneHCID 669191884-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

생성물 1

HCID 575154594-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol수율 69.2%

시약·촉매·용매 2

HCID 10176127Pyridinium chloride촉매HCID 1140Toluene용매

실험 절차

Trimethylorthobutyrate (1.9 mL, 12.0 mmol) and pyridine hydrochloride (23 mg, 0.2 mmol) were added to a suspension of 4-[(3-amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the resulting solid was isolated by filtration to provide 2.26 g of 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. customthe resulting solid was isolated by filtration

출처 및 근거

ORD 기록
ord-ee4d7896f3c94d31bfbdef497c42ae6c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541438B2

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