Potassium Phosphate, Tribasic → 4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-N-(2-dimethylaminoethyl)benzamide

HRID 908374Notes

Reaction equation

HRID 908374 reaction equation
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:29]1[CH:30]=[C:31]([C:36]2[O:37][C:38]3[C:39]([N:44]=2)=[N:40][CH:41]=[CH:42][CH:43]=3)[C:32]([NH2:35])=[N:33][CH:34]=1.[CH3:45][N:46]([CH3:67])[CH2:47][CH2:48][NH:49][C:50](=[O:66])[C:51]1[CH:56]=[CH:55][C:54](B2OC(C)(C)C(C)(C)O2)=[CH:53][CH:52]=1>O1CCOCC1.O>[NH2:35][C:32]1[N:33]=[CH:34][C:29]([C:54]2[CH:55]=[CH:56][C:51]([C:50]([NH:49][CH2:48][CH2:47][N:46]([CH3:45])[CH3:67])=[O:66])=[CH:52][CH:53]=2)=[CH:30][C:31]=1[C:36]1[O:37][C:38]2[C:39]([N:44]=1)=[N:40][CH:41]=[CH:42][CH:43]=2

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2758503N-(2-dimethylaminoethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 673883775-Bromo-3-(oxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine

Product 1

HCID 673885164-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-N-(2-dimethylaminoethyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The following conditions were used. Tris(dibenzilideneacetone)dipalladium (47.2 mg), tricyclohexylphosphine (28.9 mg) and potassium phosphate (656 mg) were added to a degassed solution of 5-bromo-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (300 mg, 1.03 mmol), N-(2-dimethylaminoethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (361 mg, 1.13 mmol) in 1,4-dioxane (2 ml) and water (0.400 ml) under nitrogen atmosphere. The suspension was stirred at 90° C. for 4 hours. The mixture was filtered and the solvent was removed. The mixture was adsorbed on silica gel, the crude product was purified by flash chromatography on silica gel eluting with 10% methanol in dichloromethane follow by 10% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-N-(2-dimethylaminoethyl)benzamide after stirring overnight in acetonitrile. NMR Spectrum: (DMSO-d6) 2.19 (s, 6H), 2.42 (t, 2H), 3.35-3.42 (m, 2H), 7.50 (dd, 1H), 7.84 (d, 2H), 7.91 (bs, 2H), 7.95 (d, 2H), 8.26 (dd, 1H), 8.45 (t, 1H), 8.56 (dd, 1H), 8.61 (d, 1H), 8.73 (d, 1H); Mass spectrum: M+H+ 403

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed
  3. customthe crude product was purified by flash chromatography on silica gel eluting with 10% methanol in dichloromethane
  4. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-4622e197dbeb4482b085d7b70e543015
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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