4-Methylbenzaldehyde → [3-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-3-(4-methyl-benzylamino)-propyl]-carbamic acid tert-butyl ester

HRID 1348805노트

반응식

HRID 1348805 반응식
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH:10]([NH2:30])[C:11]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:28])[C:18]2[C:13](=[CH:14][C:15]([Cl:29])=[CH:16][CH:17]=2)[N:12]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:41]1([CH3:49])[CH:46]=[CH:45][C:44]([CH:47]=O)=[CH:43][CH:42]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH:10]([C:11]1[N:20]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:19](=[O:28])[C:18]2[C:13](=[CH:14][C:15]([Cl:29])=[CH:16][CH:17]=2)[N:12]=1)[NH:30][CH2:49][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 77254-MethylbenzaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 69226423[3-Amino-3-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 69178479[3-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-3-(4-methyl-benzylamino)-propyl]-carbamic acid tert-butyl ester수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Formula 107 where R1, R2, R4, R6, R7, R8 and R9 are H: R3 is Chloro; R5 is Benzyl; and R10 is p-Methyl-benzyl: To a solution of [3-amino-3-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-propyl]-carbamic acid tert-butyl ester (700 mg, 1.58 mmol) and DIEA (275 μL, 2.37 mmol) in 50 mL of DCM was added p-tolualdehyde (188 μL, 1.58 mmol). The mixture was stirred for 1 hour, after which sodium triacetoxyborohydride (500 mg, 2.37 mmol) was added. After stirring an additional 3 hours, the mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate. The solvents were evaporated to dryness and the residue was purified by flash silica gel chromatography (stepwise gradient 1:4, 1:2, 1:1, 2:1, 4:1 with ethyl acetate:hexanes as eluent) to give the corresponding, pure compound of Formula 107, [3-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-3-(4-methyl-benzylamino)-propyl]-carbamic acid tert-butyl ester (760 mg, 88%).

후처리

  1. stirringAfter stirring an additional 3 hours
  2. washthe mixture was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were evaporated to dryness
  5. customthe residue was purified by flash silica gel chromatography (stepwise gradient 1:4, 1:2, 1:1, 2:1, 4:1 with ethyl acetate

출처 및 근거

ORD 기록
ord-0f4dafbc8a274237bd4c99d8c2a21447
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211580B2

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