Ethyl Acetate → 4-(2-(Thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzonitrile

HRID 335178Notes

Reaction equation

HRID 335178 reaction equation
CC([O-])(C)C.[K+].[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[S:9][C:8]=1[NH:16][C:17]1[C:22]([S:23][CH2:24][CH2:25][C:26](OC)=O)=[CH:21][CH:20]=[CH:19][N:18]=1.FC1C=C[C:34]([C:35]#[N:36])=[CH:33][CH:32]=1.C(OCC)(=O)C>CS(C)=O>[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[S:9][C:8]=1[NH:16][C:17]1[C:22]([S:23][C:24]2[CH:32]=[CH:33][C:34]([C:35]#[N:36])=[CH:26][CH:25]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 145174-FluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 86631505Methyl 3-(2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate

Product 1

HCID 577428444-(2-(Thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzonitrileYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Added potassium 2-methylpropan-2-olate (0.097 g, 0.87 mmol) to a solution of methyl 3-(2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate (100 mg, 0.289 mmol) in DMSO (1 mL). Stirred 15 minutes, added 4-fluorobenzonitrile (0.105 g, 0.866 mmol) and stirred overnight. Partitioned between ethyl acetate and water. Washed the organic layer with water, brine, dried, and concentrated. Purified by MPLC eluting with 3:2 hexane:ethyl acetate to afford the title compound (0.034 g, 33% yield) as a white powder: 1H NMR (CDCl3). 7.10-7.15 (m, 3H), 7.32 (dd, 1H), 7.52 (d, 2H), 7.87 (d, 1H), 7.96 (d, 1H), 8.42 (d, 1H), 8.58 (d, 1H), 9.10 (bs, 1H).

Workup

  1. stirringstirred overnight
  2. customPartitioned between ethyl acetate and water
  3. washWashed the organic layer with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customPurified by MPLC
  7. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-6b4e7326a18e47b8bc653102daf99bd3
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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