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N-(5-amino-4-fluoro-2-methylphenyl)acetamide → N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-4-fluoro-2-methylphenyl]acetamide

HRID 606
ノート
印刷プレビュー

反応式

HRID 606 の反応式
CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c(F)cc1C
参加物反応条件実験手順出典と根拠反応ノート

参加物

7

反応物 2

HCID 89099132N-(5-amino-4-fluoro-2-methylphenyl)acetamideHCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

生成物 1

HCID 72163926N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-4-fluoro-2-methylphenyl]acetamide収率 20.63%

試薬・触媒・溶媒 4

HCID 10796Cesium carbonate試薬
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

In 20 ml microwave vial were added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (164 mg, 0.90 mmol), Pd2dba3 (39.2 mg, 0.04 mmol), di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (37.5 mg, 0.09 mmol) and Cs2CO3 (837 mg, 2.57 mmol). The vessel was fitted with septum, gas inlet and dioxane (8 mL) was added via syringe. The resulting suspension was stirred for 5 min. under N2. The septum and gas inlet quickly replaced with microwave vial cap and the mixture was heated to 150oC under microwave irradiation for 30 min. The reaction mixture filtered through celite, filtrate concentrated, combined with EN02368-53 experiment and purified by ISCO column (0-5% MeOH-CH2Cl2). The obtained compound triturated with CH3CN, filtered and dried to give light brown color solid. Conclusion: product isolated

出典と根拠

ORDレコード
ord-71ad501d78264f9aa8b8fb6c66e7e044
出典データセット
750 AstraZeneca ELN dataset
元リンク
出典を表示

反応ノート

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