Sodium cyanoborohydride → HCID 86691844, compound

HRID 1616230Notes

Reaction equation

HRID 1616230 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:26])=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH3:25])[C:17](=[O:24])[N:18]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]3=[CH:12][CH:11]=2)[CH:9]=1)(=O)[CH3:2].[NH:27]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]1.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1.CO.[Ti](Cl)(Cl)(Cl)Cl>[CH3:22][C:20]([CH3:23])([CH3:21])[CH2:19][N:18]1[C:13]2[C:14](=[N:15][C:10]([C:8]3[CH:9]=[C:4]([C@H:1]([N:27]4[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]4)[CH3:2])[CH:5]=[CH:6][C:7]=3[CH3:26])=[CH:11][CH:12]=2)[N:16]([CH3:25])[C:17]1=[O:24]

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6484228Thiomorpholine 1,1-dioxideHCID 86691837HCID 86691837, compound

Product 1

HCID 86691844HCID 86691844, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a microwave vial was added 5-(5-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (15-7) (30 mg, 0.085 mmol) and thiomorpholine 1,1-dioxide (17 mg, 0.13 mmol) were added under nitrogen and dissolved in toluene (0.43 ml). Titanium(IV) chloride (10 mg, 0.05 mmol) was added to the solution and the reaction was allow to stir at room temperature overnight. Sodium cyanoborohydride (8 mg, 0.12 mmol) was then added and allowed to stir for 1 hour. 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 1-(2,2-dimethylpropyl)-5-{5-[(1R)-1-(1,1-dioxidothiomorpholin-4-yl)ethyl]-2-methylphenyl}-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (36-1). HRMS (M+H)+: observed=471.2421, calculated=471.2424.

Workup

  1. additionwere added under nitrogen
  2. stirringto stir for 1 hour
  3. custompassed through a syringe
  4. filtrationfilter
  5. customThe solution was purified
  6. customthe desired fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f4e0dd76bf21485b98bea3d70644e999
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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