Isobutyl chloroformate → HCID 86762489, compound

HRID 1616223Notes

Reaction equation

HRID 1616223 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]3[N:15]([CH3:24])[C:16](=[O:23])[N:17]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]3=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl[C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27].C(N(C(C)C)CC)(C)C>C1COCC1.CO>[CH3:22][C:19]([CH3:21])([CH3:20])[CH2:18][N:17]1[C:12]2[C:13](=[N:14][C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[CH2:2][NH:1][C:26](=[O:27])[O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:10][CH:11]=2)[N:15]([CH3:24])[C:16]1=[O:23]

Participants

6

Reactant 3

HCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 86691833HCID 86691833, compound

Product 1

HCID 86762489HCID 86762489, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a microwave vial, 5-[3-(aminomethyl)phenyl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (23-1) (15 mg, 0.05 mmol) was added under nitrogen and dissolved in THF (0.25 ml). Isobutyl chloroformate (4.4 mg, 0.055 mmol) was added followed by diisopropyl ethyl amine 9 mg, 0.07 mmol). The reaction was allowed to stir for 2 hours at room temperature. The reaction was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-methylpropyl {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzyl}carbamate (23-2). HRMS (M+H)+: observed=425.2549, calculated=425.2547.

Workup

  1. custompassed through a syringe
  2. filtrationfilter
  3. customThe solution was purified
  4. customthe desired fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4fc2a9a5e2144ad85732086d73c5090
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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