1,1'-Carbonyldiimidazole → HCID 59526207, compound

HRID 385897Notes

Reaction equation

HRID 385897 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:24][N:25]1[CH:29]=[C:28]([NH2:30])[CH:27]=[N:26]1>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([NH:30][C:28]2[CH:27]=[N:26][N:25]([CH3:24])[CH:29]=2)=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 47709901-methyl-1H-pyrazol-4-amineHCID 468357142-(6-Bromopyridin-2-yl)acetic acid

Product 1

HCID 59526207HCID 59526207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (6-bromopyridin-2-yl)acetic acid (Example 235, Step 2) (30 mg, 0.39 mmol) in dimethylformamide (3 mL) was charged with carbonyldiimidazole (338 mg, 2.08 mmol) and maintained at room temperature for 1 hour. A solution of 1-methyl-1H-pyrazol-4-amine (175 mg, 1.81 mmol) in dimethylformamide (2 mL) was added and the reaction was stirred overnight at room temperature. The reaction was then directly purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to yield the title compound.

Workup

  1. customThe reaction was then directly purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-60b7cc9f327c4e61927dc937b5a2c69a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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