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HCID 178418203, 화합물 → N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide

HRID 696
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인쇄 미리보기

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HRID 696 반응식
CC(=O)Nc1cc(N)c(F)cc1C1CC1.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)c(F)cc1C1CC1
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참가 물질

7

반응물 2

HCID 178418203HCID 178418203, 화합물HCID 178418222HCID 178418222, 화합물

생성물 1

HCID 72164290N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide수율 3.55%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane촉매
HCID 31374Dimethylacetamide용매

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온도
145 °C

실험 절차

In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (0.167 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 giveN-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropyl-4-fluorophenyl)acetamide (0.012 g, 3.55 %) LCMS and NMR were OK, see attachment.

출처 및 근거

ORD 기록
ord-bfef1bef76ff43f7a429af888b0d1628
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
출처 보기

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