Isopropylamine → 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-5-carboxylic acid isopropylamide

HRID 245647ノート

反応式

HRID 245647 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](=[N:19][CH:20]=[CH:21][CH: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(#N)C.O.[CH:36]([NH2:39])([CH3:38])[CH3:37]>[Cl-].[Na+].O>[CH:36]([NH:39][C:25]([C:24]1[C:23]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]=2[CH:17]=[CH:16][C:15]=1[NH:14][C:13]([C:12]1[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=[C:10]([C:28]([F:31])([F:29])[F:30])[CH:11]=1)=[O:26])=[O:27])([CH3:38])[CH3:37]

参加物

5

反応物 3

HCID 6363IsopropylamineHCID 18373917Acetonitrile--water (1/1)HCID 579901052-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one

生成物 1

HCID 579901556-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-5-carboxylic acid isopropylamide収率 66.3%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

To a suspension of 150 mg (0.30 mmol) of the above 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one in 6 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 78 μL (0.91 mmol) of isopropylamine. 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/ethyl acetate 1:1) affords 100 mg (65%) of a white solid; LC/MS:503/505 (M+H)+, m.p.: 182-183° 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/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-b097b23e6749412daf94c5e47f72eeda
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

反応ノート

読み込み中…