Hydrochloric Acid → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641455

反応式

HRID 1641455 の反応式
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([NH:12][CH:13]([CH:15]1[CH2:17][CH2:16]1)[CH3:14])=[O:11].[Br:23][C:24]1[CH:28]=[C:27]([C:29](OCCCCC)=[O:30])[N:26]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:25]=1.Cl>CS(C)=O>[Br:23][C:24]1[CH:28]=[C:27]([C:29]([NH:7][C:8]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=2[C:10](=[O:11])[NH:12][CH:13]([CH:15]2[CH2:17][CH2:16]2)[CH3:14])=[O:30])[N:26]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:25]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 435330962-amino-5-chloro-N-(1-cyclopropylethyl)benzamideHCID 59549434pentyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

生成物 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide収率 13.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

0.11 g potassium tert-butoxide was added to a mixed solution comprising 0.19 g of 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide, 0.30 g of pentyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate and 3 ml of dimethyl sulfoxide, followed by reaction at room temperature for 45 minutes. The reaction liquid was slowly added to 40 ml of diluted hydrochloric acid. The mixed liquid was subjected to extraction with ethyl acetate, and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7.5/2.5) to obtain 0.058 g of the desired product (melting point: 231 to 233° C.) in the form of white crystals.

後処理

  1. customfollowed by reaction at room temperature for 45 minutes
  2. customThe reaction liquid
  3. extractionThe mixed liquid was subjected to extraction with ethyl acetate
  4. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and with a sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7.5/2.5)

出典と根拠

ORDレコード
ord-64b25188dd7c4f9b9b2f10ce2c1320db
出典データセット
uspto-grants-2012_02
特許番号
US08115006B2

関連ノート

読み込み中…