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

HRID 1398498Notes

Reaction equation

HRID 1398498 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-d5c3b52c8ea54c14bc32e3de9d4462ac
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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