Diisopropylethylamine → HCID 86691841, compound

HRID 1616227Notes

Reaction equation

HRID 1616227 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([C@@H:21]([OH:23])[CH3:22])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CS(C)=O.CO>[C:21]([C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:9]2[N:8]=[C:7]3[N:6]([CH3:24])[C:5](=[O:25])[N:4]([CH2:3][C:2]([CH3:26])([CH3:1])[CH3:27])[C:12]3=[CH:11][CH:10]=2)[CH:20]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 86691840HCID 86691840, compound

Product 1

HCID 86691841HCID 86691841, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a microwave vial, 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-[1-hydroxyethyl]benzonitrile (30-2) (35 mg, 0.1 mmol) was dissolved in DCM (0.25 ml) under nitrogen, followed by the addition of Diisopropyl ethyl amine (50 mg, 0.39 mmol). In a separate vial under nitrogen, SO3 Pyridine complex (61 mg, 0.39 mmol) was dissolved in DMSO (0.25 ml). The DMSO solution was then added slowly to DCM solution and allowed to stir at room temperature. After 30 minutes, the mixture 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 4-acetyl-2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzonitrile (31-1). HRMS (M+H)+: observed=363.1832, calculated=363.1816.

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-2235a86595b24d01817659104f58dfa1
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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