Sodium Carbonate → (S)-tert-butyl (1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 2284774노트

반응식

HRID 2284774 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[C:8]([NH:14][CH2:15][CH2:16][CH3:17])=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1.[C:18]([N:25]([CH3:31])[C@H:26]([C:28](O)=[O:29])[CH3:27])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:13][C:10]1[N:9]=[C:8]([NH:14][CH2:15][CH2:16][CH3:17])[C:7]([C:6]#[C:5][CH2:4][CH2:3][CH2:2][NH:1][C:28](=[O:29])[C@@H:26]([N:25]([CH3:31])[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH3:27])=[CH:12][N:11]=1

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 900521545-(5-amino-1-pentyn-1-yl)-2-chloro-N-propylpyrimidin-4-amine

생성물 1

HCID 90052304(S)-tert-butyl (1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate수율 113.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(5-amino-1-pentyn-1-yl)-2-chloro-N-propylpyrimidin-4-amine (K2, 505 mg) and N-Boc-N-methyl-L-alanine (270 mg) in N,N-dimethylformamide (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (635 mg) and N,N-diisopropylethylamine (378 μL) were added at room temperature, and the mixture was stirred overnight at the same temperature. To the reaction mixture, saturated aqueous sodium carbonate and ethyl acetate were added. The organic layer was separated, washed with water, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 50% hexane/50% ethyl acetate) to obtain (S)-tert-butyl (1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (L1, 660 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 50% hexane/50% ethyl acetate)

출처 및 근거

ORD 기록
ord-f9d88be0d8bf486b84af3da3c1e8571e
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145415B2

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