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Sodium hydride → 1-{4-[(2-methoxypyridin-3-yl)amino]-1,3,5-triazin-2-yl}-1H-indazole-6-carbonitrile

HRID 1398498
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HRID 1398498 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].Cl[C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]2[C:23]([O:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=2)[N:16]=1>CN(C=O)C>[CH3:29][O:28][C:23]1[C:22]([NH:21][C:17]2[N:16]=[CH:15][N:20]=[C:19]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=4)[CH:3]=[N:2]3)[N:18]=2)=[CH:27][CH:26]=[CH:25][N:24]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 4225291H-indazole-6-carbonitrileHCID 866695704-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

생성물 1

HCID 601641631-{4-[(2-methoxypyridin-3-yl)amino]-1,3,5-triazin-2-yl}-1H-indazole-6-carbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1H-indazole-6-carbonitrile (70 mg, 0.49 mmol) in DMF (5 mL) was added NaH (60% oil dispersion, 39.12 mg, 0.98 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes before the addition of 4-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine (139.45 mg, 0.59 mmol). Stirring at RT was continued for 2 hr. The reaction mixture was then quenched with water and EtOAc was added. Precipitate formed was collected by suction filtration, then redissolved in DCM and washed with water. Further trituration (9:1 mixture of heptane/Et2O) gave the title compound: 1H (250 MHz, CDCl3, VT @ 323K) δ 4.10 (3H, s), 7.06 (1H, br. s.), 7.60 (1H, dd, J=8.22, 1.37 Hz), 7.91 (1H, dd, J=8.22, 0.76 Hz), 7.97 (2H, d), 8.42 (1H, d, J=0.76 Hz), 8.74 (1H, dd, J=7.84, 1.60 Hz), 8.86 (1H, s), 9.20 (1H, s); m/z=+345.0 (M+H)+.

후처리

  1. customThe reaction mixture was then quenched with water and EtOAc
  2. additionwas added
  3. customPrecipitate formed
  4. filtrationwas collected by suction filtration
  5. dissolutionredissolved in DCM
  6. washwashed with water
  7. additionFurther trituration (9:1 mixture of heptane/Et2O)

출처 및 근거

ORD 기록
ord-d5c3b52c8ea54c14bc32e3de9d4462ac
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901313B2

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