1,3-Dimethyl-1H-pyrazol-5-amine → 2-(2-(1,3-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide
Reaction equation
CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC.Cc1cc(N)n(C)n1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OCParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 90 °C
Procedure
_2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide (1.66 g, 4.61 mmol)_ _,_ _1,3-dimethyl-1H-pyrazol-5-amine (0.523 g, 4.71 mmol)_ _,_ _diacetoxypalladium (0.083 g, 0.37 mmol)_ _,_ _(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.427 g, 0.74 mmol)_ _and_ _cesium carbonate (1.804 g, 5.54 mmol)_ _were mixed together in_ _dioxane (30 mL)_ _. Reaction was degassed with argon and was stirred at_ _90 °C_ _for 3 hours under argon.The mixture was filtered ,the filtrate was concentrated and purified by flash chromatography on silica gel 15-40µm eluting with __0_ _to_ _4_ _% methanol in CH2Cl2/AcOEt (60/40).The product obtained was not enough pure so the product was repurified by flash chromatography on silica gel 15-40µm eluting with 0 to 4% methanol in CH2Cl2/AcOEt (60/40).The solvent was evaporated to dryness to afford _2-(2-(1,3-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy- N-methylbenzamide (0.882 g, 44.0 %) _as a _beige __ solid _._ _EN 02814-27-01_
Sources & evidence
- ORD record
- ord-ffcc436f225c440ca5c8c1a40df255a3
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
Loading…