N-(5-amino-2-cyclopropylphenyl)acetamide → N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide

HRID 738ノート

反応式

HRID 738 の反応式
CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>CC(=O)N(C)C.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(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1

参加物

7

反応物 2

HCID 89098640N-(5-amino-2-cyclopropylphenyl)acetamideHCID 178418222HCID 178418222、化合物

生成物 1

HCID 72164289N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide収率 8.66%

試薬・触媒・溶媒 4

HCID 10796Cesium carbonate試薬HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
145 °C

実験手順

In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropylphenyl)acetamide (0.152 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08 mmol). anhydrous DMA (1.0 mL) was added. The resulting mixture was bubbled through N2. Then the tube was capped. under microwave 145C for 25min. LCMS showed product and byproduct mass, did not showed SM The mixture was filtered through celite. The resulting black solution was concentrated to dryness by rotavapor. The crude product was purified by ISCO (40g, Hex to EtOAc:HEx=1;2 to 1;1 to EtOAcO) to give product (offwhite solid). HPLC showed some impurity. This offwhite solid was washed with warm EtOAc (1mL) to give N-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropylphenyl)acetamide (0.028 g, 8.66 %). LCMS and NMR were OK< see attachment.

出典と根拠

ORDレコード
ord-475c89db99fe4f418713bc4636a30c0a
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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