Isobutyryl chloride → HCID 178454485, compound

HRID 2064631Notes

Reaction equation

HRID 2064631 reaction equation
C[O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[NH:9][C:10]([C:12]3[C:16]([NH2:17])=[CH:15][NH:14][N:13]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].C(N(C(C)C)CC)(C)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>O1CCCC1>[C:29]([NH:17][C:16]1[C:12]([C:10]2[NH:9][C:8]3[CH:18]=[CH:19][C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]=3[N:11]=2)=[N:13][NH:14][CH:15]=1)(=[O:33])[CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 178497353HCID 178497353, compound

Product 1

HCID 178454485HCID 178454485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-amino-1H-pyrazol-3-yl)-1H-benzoimidazole-5-carboxylic acid methyl ester [200 mg, Example 233(k)] in tetrahydrofuran (5 ml) was added diisopropylethylamine (545 μl) and isobutyryl chloride (327 μl) dropwise and the reaction stirred for 30 minutes. The reaction mixture was concentrated in vacuo and the residue was taken up in 1M potassium hydroxide in tetrahydrofuran/methanol (1:3, v/v) (5 ml) and stirred for 1 hour. The reaction mixture was concentrated in vacuo and the residue was taken up in 1M sodium hydroxide in water/methanol (5 ml) and stirred for 1 hour. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water and the layers separated. The aqueous layer was acidified to pH 3-4 with 5% citric acid solution, extracted with ethyl acetate and the organic layer washed with brine. The organic layer was then dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to give 2-(4-isobutyrylamino-1H-pyrazol-3-yl)-1H-benzoimidazole-5-carboxylic acid (140 mg) as a white solid. LC-MS (METHOD C): RT=2.87 minutes, 313.33 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. stirringv/v) (5 ml) and stirred for 1 hour
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. stirringstirred for 1 hour
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between ethyl acetate and water
  7. customthe layers separated
  8. extractionextracted with ethyl acetate
  9. washthe organic layer washed with brine
  10. dry with materialThe organic layer was then dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5e26fce6431144c89fd4b91da1777094
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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