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1,3-dimethyl-1H-pyrazol-4-amine → 2-({5-Chloro-2-[(1,3-dimethyl-1h-pyrazol-4-yl)amino]-4-pyridinyl}amino)-n-methylbenzamide

HRID 61
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HRID 61 반응식
CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1nn(C)cc1N>C1CCCC1.CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.COCCOC.[Fe].[Na+].[Pd]>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1Cl
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참가 물질

7

반응물 2

HCID 44310561,3-dimethyl-1H-pyrazol-4-amineHCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

생성물 1

HCID 446098242-({5-Chloro-2-[(1,3-dimethyl-1h-pyrazol-4-yl)amino]-4-pyridinyl}amino)-n-methylbenzamide수율 53.31%

시약·촉매·용매 4

HCID 23676156Sodium t-butoxide시약HCID 4144353Palladium (II) acetate
촉매
HCID 144543273(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-촉매
HCID 80711,2-Dimethoxyethane용매

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온도
150 °C

실험 절차

1,3-dimethyl-1H-pyrazol-4-amine (180 mg, 1.62 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (400 mg, 1.35 mmol), Sodium t-Butoxide (156 mg, 1.62 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (73.8 mg, 0.14 mmol) and diacetoxypalladium (24.26 mg, 0.11 mmol) were suspended in DME (8 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Incomplete reaction, the reaction was heated to 150 °C for a further 1 hour in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was then purified by Basic prep HPLC, fractions containing the desired compound were evaporated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (267 mg, 53.3 %) as a brown solid.

출처 및 근거

ORD 기록
ord-23579b28ef824d8ba8083ac0e9a7b70a
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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