alpha-Methyl-DL-leucine → 4-(3-Methyl-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)-benzylamine

HRID 1678744노트

반응식

HRID 1678744 반응식
[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[NH2:29]C(C)(CC(C)C)C(O)=O>CN(C=O)C>[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH2:19][NH2:29])=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1

참가 물질

4

반응물 2

HCID 95515alpha-Methyl-DL-leucineHCID 594729414-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde

생성물 1

HCID 159792734-(3-Methyl-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)-benzylamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A suspension of 4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (13, 0.25 g, 0.69 mmol) and 2-amino-2,4-dimethylpentanoic acid (3-7, 0.101 g, 0.69 mmol) in DMF (3 mL) was heated at 150° C. for 30 min. The reaction mixture cooled and the solvent was removed in vacuo. The crude residue was dissolved in 3N HCl (2.5 mL) and was heated at 100° C. for 30 min. The mixture was cooled and purified via reverse phase HPLC (5-65% acetonitrile/water over 15 min) to give, upon evaporation of the solvents, the title compound as a yellow solid. HRMS m/z (M+1) Calcd: 366.1713. Found 366.1715.

후처리

  1. temperatureThe reaction mixture cooled
  2. customthe solvent was removed in vacuo
  3. dissolutionThe crude residue was dissolved in 3N HCl (2.5 mL)
  4. temperaturewas heated at 100° C. for 30 min
  5. temperatureThe mixture was cooled
  6. custompurified via reverse phase HPLC (5-65% acetonitrile/water over 15 min)
  7. customto give, upon evaporation of the solvents

출처 및 근거

ORD 기록
ord-fb4fe4861f764e7c8c41baa918afdfa4
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008317B2

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