Methylamine → 7-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid methylamide

HRID 245643ノート

反応式

HRID 245643 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:26][C:25](=[O:27])[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][N:22]=5)[CH:17]=[CH:16][C:15]=4[N:14]=3)=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:32](#[N:34])C.O.CN>[Cl-].[Na+].O>[CH3:32][NH:34][C:25]([C:24]1[C:15]([NH:14][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:28]([F:30])([F:31])[F:29])[CH:11]=2)=[O:26])=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)=[O:27]

参加物

5

反応物 3

HCID 6329MethylamineHCID 18373917Acetonitrile--water (1/1)HCID 579901522-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one

生成物 1

HCID 579901137-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid methylamide収率 62%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

To a suspension of 140 mg (0.28 mmol) of the above 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one in 5.60 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 74 μL (0.85 mmol) of methylamine (solution 40% in water). The reaction mixture is stirred for 6 hours at ambient temperature. Brine is then added to the mixture and the product is extracted with ethyl acetate (3 times). The regrouped organic phases are dried on Na2SO4, filtrated and evaporated. The purification of the residue by flash chromatography (SiO2, heptane and ethyl acetate as eluants) affords 84 mg (62%) of a white solid; LC/MS:475/477 (M+H)+, m.p.: 219-220° C.

後処理

  1. extractionthe product is extracted with ethyl acetate (3 times)
  2. customThe regrouped organic phases are dried on Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe purification of the residue by flash chromatography (SiO2, heptane and ethyl acetate as eluants)

出典と根拠

ORDレコード
ord-cb988c8285f342008f9de480813b788e
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

反応ノート

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