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Sodium Bicarbonate → 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(3-(2,2,2-trifluoro-N-methylacetamido)phenyl)pyrimidine-5-carboxamide

HRID 2284638
ノート
印刷プレビュー

反応式

HRID 2284638 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:15])[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][CH:7]=1.[CH2:16]([NH:19][C:20]1[C:25]([C:26](O)=[O:27])=[CH:24][N:23]=[C:22]([NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[N:21]=1)[CH2:17][CH3:18].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH2:16]([NH:19][C:20]1[C:25]([C:26]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N:8]([CH3:15])[C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[CH:3]=2)=[O:27])=[CH:24][N:23]=[C:22]([NH:29][CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)[N:21]=1)[CH2:17][CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22946301N-(3-aminophenyl)-2,2,2-trifluoro-N-methylactamideHCID 900517164-(Propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid

生成物 1

HCID 90052002
4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(3-(2,2,2-trifluoro-N-methylacetamido)phenyl)pyrimidine-5-carboxamide
収率 26.8%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To N-(3-aminophenyl)-2,2,2-trifluoro-N-methylactamide (302 mg) synthesized according to the method described in U.S. Pat. No. 6,344,465 B1, 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid (A3, 627 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (545 mg) and 1-hydroxybenzotriazole monohydrate (377 mg), N,N-dimethylformamide (15 mL) and triethylamine (766 μL) were added at room temperature, the reaction vessel was sealed, and then the mixture was stirred at 100° C. for 40 minutes by using a microwave reaction system. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the mixture. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 97 to 96% ethyl acetate in methanol) to obtain 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(3-(2,2,2-trifluoro-N-methylacetamido)phenyl)pyrimidine-5-carboxamide (A7, 186 mg).

後処理

  1. customthe reaction vessel was sealed
  2. customa microwave reaction system
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent, 97 to 96% ethyl acetate in methanol)

出典と根拠

ORDレコード
ord-00da24b1dcc84df0b3c1cb3284d9ab60
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145415B2

反応ノート

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