Imidazole → HCID 89524439, compound

HRID 571398Notes

Reaction equation

HRID 571398 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.C1N=CN([C:36](N2C=NC=C2)=[O:37])C=1.N1C=CN=C1.[C:48]1([C@H:54]([NH2:56])[CH3:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:36]([NH:56][C@@H:54]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH3:55])=[O:37])=[CH:10][C:5]=2[N:4]([C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 6431891-Phenethylamine, (+)-HCID 89526503HCID 89526503, compound2×

Product 1

HCID 89524439HCID 89524439, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (Intermediate 9a, 500 mg, 1.098 mmol), CDI (356 mg, 2.196 mmol), imidazole (150 mg, 2.196 mmol) and DCM (11 mL) were charged in a flask. The mixture was stirred at room temperature for 16 h and then treated with (R)-1-phenylethanamine (272 mg, 2.245 mmol). The mixture was stirred at room temperature for 1 h and then purified by chromatography on silica gel (EtOAc in hexane, 0-40%, 25 CV) to afford (R)-1-(3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (582 mg, 0.966 mmol, 88%) as a white solid. MS ESI calcd. For C34H29BrN5O [M+H]+ 602, found 602.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. custompurified by chromatography on silica gel (EtOAc in hexane, 0-40%, 25 CV)

Sources & evidence

ORD record
ord-9f9e83b3e9444deb81271db4cf5acf13
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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