Imidazole → HCID 22727459, compound

HRID 2085958Notes

Reaction equation

HRID 2085958 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:8]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[C:26]4[CH:34]=[C:33](Cl)[N:32]=[CH:31][C:27]=4[N:28]=[CH:29][N:30]=3)=[CH:21][CH:22]=2)[CH:17]=[N:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CS(C)=O>[CH2:8]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]3[C:26]4[CH:34]=[C:33]([N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)[N:32]=[CH:31][C:27]=4[N:28]=[CH:29][N:30]=3)=[CH:21][CH:22]=2)[CH:17]=[N:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 21952012(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine

Product 1

HCID 22727459HCID 22727459, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Imidazole (0.8 g) in dry DMSO was treated with sodium hydride (60%, 0.47 g) and (1-Benzyl-1H-indazol-5-yl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine in a reacti-vial and heated at 120° C. After 7 days, the mixture was poured onto water and extracted with ethyl acetate. Purification using a Bond Elute™ cartridge gave the title compound as a brown solid after trituration from water; δH [2H6]DMSO 10.28(1H,s), 9.25(1H,s), 8.90(1H,s), 8.78(1H,s), 8.67(1H,s), 8.40(1H,s), 8.30(1H,s), 8.10(1H,s), 7.88(2H,m), 7.40(5H,m), 5.70(2H,s); m/z (M+) 419.

Workup

  1. additionthe mixture was poured onto water
  2. extractionextracted with ethyl acetate
  3. customPurification
  4. washElute™ cartridge

Sources & evidence

ORD record
ord-8a2dd822a4ed491a8ea4ddac78636add
Source dataset
uspto-grants-2004_04
Patent number
US06723726B1

Reaction notes

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