تفاعل #90782

معادلة التفاعل

2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide

1,3-dimethyl-1H-pyrazol-4-amine

cesium carbonate

BINAP

→

desired product

المردود 18.0%

2-({5-Chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide

المردود 18.0%

المذيبات

dioxane THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was degassed under nitrogen for 10 min
2. 2
   أخرىIt was evaporated
3. 3
   workup.DISSOLUTIONthe residue dissolved in MeOH
4. 4
   ترشيحwas filtered thru celite
5. 5
   أخرىpurified further
6. 6
   أخرىevaporated
7. 7
   workup.ADDITIONEther was added to the residue
8. 8
   ترشيحIt was filtered off
9. 9
   أخرىdried under vacuum at 40° C. for 2 days

الإجراء التجريبي

A microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (250 mg, 0.8 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (187 mg, 1.68 mmol), cesium carbonate (783 mg, 2.4 mmol) and dioxane/THF (3:1 ml). The reaction mixture was degassed under nitrogen for 10 min and palladium (II) acetate (9 mg, 0.04 mmol) and BINAP (50 mg, 0.08 mmol) were added. The mixture was stirred in a microwave at 140° C. for 40 min. It was evaporated and the residue dissolved in MeOH was filtered thru celite and thru an Acrodisc and purified further using preparative Agilent HPLC (5 to 95% water:acetonitrile with 0.1% formic acid). Fractions were combined and evaporated. Ether was added to the residue and a tan precipitate crashed out. It was filtered off and dried under vacuum at 40° C. for 2 days to afford the desired product (55 mg, 18%) as a tan solid. LC-MS (ES) m/z=387.1, [M+H]+=389.1. 1H NMR (400 MHz, DMSO-d6) ppm 11.93 (br. s., 1 H) 9.51 (br. s., 1 H) 8.03 (s, 1 H) 7.96 (s, 1 H) 7.82 (s, 1 H) 7.51-7.61 (m, 3 H) 7.07-7.15 (m, 1 H) 6.68 (s, 1 H) 3.70 (d, J=4.29 Hz, 6 H) 2.07 (s, 3 H).

المصدر