Diisopropylethylamine → N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

HRID 888163노트

반응식

HRID 888163 반응식
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:21])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3F)=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][C:31]([CH2:32][NH2:33])=[C:26]2[CH:25]=[N:24]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([C:14]3[C:15]([NH:33][CH2:32][C:31]4[CH:30]=[CH:29][N:28]=[C:27]5[NH:23][N:24]=[CH:25][C:26]=45)=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:21])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 81531Diisopropylethylamine2회HCID 55285368(1H-Pyrazolo[3,4-b]pyridin-4-yl)methanamine2회HCID 68908856N-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-fluoro-nicotinamide

생성물 1

HCID 58942003N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

N-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-fluoro-nicotinamide (60 mg, 0.201 mmol) was dissolved in NMP (0.5 mL), then C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (36 mg, 0.243 mmol) and DIEA (70 μL, 0.401 mmol) were added. The mixture was heated at 120° C. overnight. Additional C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (14 mg, 0.094 mmol) and DIEA (35 μL, 0.200 mmol) were added and the mixture was heated at 120° C. overnight. The mixture was partitioned between water and EtOAc. The mixture was diluted with EtOAc then washed with water and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2) to give N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide as a yellow solid. MS m/e 428.2(M+H)+. Calc'd for C24H25N7O—427.51.

후처리

  1. temperaturethe mixture was heated at 120° C. overnight
  2. customThe mixture was partitioned between water and EtOAc
  3. additionThe mixture was diluted with EtOAc
  4. washthen washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification

출처 및 근거

ORD 기록
ord-73d103710e0941d49e1b3b84b416b9e1
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247556B2

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