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Methylamine → (S)-tert-butyl methyl(1-((5-(2-(methylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)carbamate

HRID 2284773
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HRID 2284773 반응식
N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:39])[C@@H:28]([N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[CH3:40][NH2:41]>O1CCCC1>[CH3:38][N:30]([C@@H:28]([CH3:29])[C:27]([NH:26][CH2:25][CH2:24][CH2:23][C:22]#[C:21][C:14]1[C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[N:16][C:11]([NH:41][CH3:40])=[N:12][CH:13]=1)=[O:39])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35]
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참가 물질

4

반응물 2

HCID 6329MethylamineHCID 90052416(S)-tert-butyl (1-((5-(2-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

생성물 1

HCID 90052155(S)-tert-butyl methyl(1-((5-(2-(methylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To (S)-tert-butyl (1-((5-(2-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (K3, 50 mg), a 2.0 mol/L solution of methylamine in tetrahydrofuran (1 mL) was added at room temperature, the reaction vessel was sealed, and then the mixture was stirred at 50° C. for 5 hours by using a microwave reaction system. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 40 to 0% hexane in ethyl acetate) to obtain oily (S)-tert-butyl methyl(1-((5-(2-(methylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)carbamate (K4, 35 mg).

후처리

  1. customthe reaction vessel was sealed
  2. customa microwave reaction system
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 40 to 0% hexane in ethyl acetate)

출처 및 근거

ORD 기록
ord-418de67864e04681bdccc7e3b3d29233
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145415B2

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