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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
ノート
印刷プレビュー

反応式

HRID 61 の反応式
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
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 44310561,3-dimethyl-1H-pyrazol-4-amineHCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

生成物 1

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

試薬・触媒・溶媒 4

HCID 23676156Sodium t-butoxide試薬HCID 4144353Palladium (II) acetate
触媒
HCID 144543273(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
150 °C

実験手順

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.

出典と根拠

ORDレコード
ord-23579b28ef824d8ba8083ac0e9a7b70a
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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