1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (S)-tert-butyl (1-((5-(2-((3-fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 2284760노트

반응식

HRID 2284760 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[C:8]([NH:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])=[N:9][C:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[N:11][CH:12]=1.[C:27]([N:34]([CH3:40])[C@H:35]([C:37](O)=[O:38])[CH3:36])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C.O>[F:20][C:16]1[CH:15]=[C:14]([NH:13][C:10]2[N:9]=[C:8]([NH:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[C:7]([C:6]#[C:5][CH2:4][CH2:3][CH2:2][NH:1][C:37](=[O:38])[C@@H:35]([N:34]([CH3:40])[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[CH3:36])=[CH:12][N:11]=2)[CH:19]=[CH:18][CH:17]=1

참가 물질

9

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 900521525-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-(3-methoxypropyl)pyrimidine-2,4-diamine

생성물 1

HCID 90052150(S)-tert-butyl (1-((5-(2-((3-fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 81531Diisopropylethylamine용매

실험 절차

To a solution of 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-(3-methoxypropyl)pyrimidine-2,4-diamine (J7, 55 mg), N-Boc-N-methyl-L-alanine (63 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (59 mg) and 1-hydroxybenzotriazole monohydrate (42 mg) in N,N-dimethylformamide (700 μL), N,N-diisopropylethylamine (108 μL) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain (S)-tert-butyl (1-((5-(2-((3-fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (J8, 84 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5791b862a45b462cb79e48a65b3e48e5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145415B2

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