Ethyl Acetate → 5-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridin-2-amine

HRID 241225노트

반응식

HRID 241225 반응식
Cl.Cl.[N+:3]([C:6]1[C:7]([NH2:23])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]=3[CH:22]=2)[CH:11]=1)([O-:5])=[O:4].Cl[C:25]1[C:34]2[CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31][CH2:30][C:29]=2[N:28]=[CH:27][N:26]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O>[CH3:35][C:32]1([CH3:36])[CH2:31][CH2:30][C:29]2[N:28]=[CH:27][N:26]=[C:25]([N:18]3[CH2:17][C:16]4[CH:22]=[C:12]([C:10]5[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]([NH2:23])=[N:8][CH:9]=5)[CH:13]=[CH:14][C:15]=4[O:21][CH2:20][CH2:19]3)[C:34]=2[CH2:33]1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 668206213-Nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochlorideHCID 866478114-Chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline

생성물 1

HCID 668203605-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridin-2-amine수율 81.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of 3-nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride (540 mg, 1.50 mmol), 4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline (270 mg, 1.37 mmol, reagent preparation 3), and diisopropylethylamine (970 mg, 7.49 mmol) in N-methylpyrrolidinone (3 mL) was stirred at 120° C. for 18 h. After cooling to room temperature ethyl acetate (100 mL) was added, the formed precipitate was filtered off, the organic filtrate was washed with saturated sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL), dried over sodium sulfate, filtered and concentrated to afford crude 5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridine-2-amine (0.5 g) as a brown solid which was used in the next step without further purification. MS (EI) for C24H26N6O3: 447 (MH+).

후처리

  1. additionwas added
  2. filtrationthe formed precipitate was filtered off
  3. washthe organic filtrate was washed with saturated sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-63be500c902b4c31a6552d488e01ab8f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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