Heptanoic Acid → 2,3-Difluoro-4-[5-(6-octyloxypyridin-3-yl)pyrimidin-2-yl]phenyl heptanoate

HRID 376774ノート

反応式

HRID 376774 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.[F:16][C:17]1[C:22]([F:23])=[C:21]([OH:24])[CH:20]=[CH:19][C:18]=1[C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:36]=2)=[CH:27][N:26]=1.[C:46](O)(=[O:53])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>CN(C1C=CN=CC=1)C.ClCCl>[C:46]([O:24][C:21]1[CH:20]=[CH:19][C:18]([C:25]2[N:30]=[CH:29][C:28]([C:31]3[CH:32]=[N:33][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:36]=3)=[CH:27][N:26]=2)=[C:17]([F:16])[C:22]=1[F:23])(=[O:53])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

参加物

6

反応物 3

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 1355974452-(2,3-Difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

生成物 1

HCID 536635672,3-Difluoro-4-[5-(6-octyloxypyridin-3-yl)pyrimidin-2-yl]phenyl heptanoate収率 84%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2.7 mmol of DCC are introduced at room temperature into 50 ml of dichloromethane, and 2.4 mmol of 2-(2,3-difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine, 2.7 mmol of heptanoic acid and 0.24 mmol of DMAP are added. The reaction mixture is left to stand overnight with exclusion of light, precipitated dicyclohexylurea is then filtered off, and the solvent is removed in vacuo. The crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent and is recrystallized from acetonitrile, giving 1.0 g (84%) of colorless crystals, X 88 SC 165 SA 167.5 I.

後処理

  1. additionare added
  2. waitThe reaction mixture is left
  3. customprecipitated dicyclohexylurea
  4. filtrationis then filtered off
  5. customthe solvent is removed in vacuo
  6. customThe crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent
  7. customis recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-639f839adc1d4fd6bd4c86c5a1614cff
出典データセット
uspto-grants-2000_02
特許番号
US06022492

反応ノート

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