m-Aminoacetanilide → N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide

HRID 75653

反応式

HRID 75653 の反応式
[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11](OS(C(F)(F)F)(=O)=O)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:26]3[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=3[F:33])[C:5]2=[O:34])[CH2:3][CH2:2]1.[NH2:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][CH:45]=1)[NH:39][C:40](=[O:42])[CH3:41].CN(C)C(=O)C.N1C(C)=CC=CC=1C>CO.O>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([NH:35][C:36]4[CH:37]=[C:38]([NH:39][C:40](=[O:42])[CH3:41])[CH:43]=[CH:44][CH:45]=4)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:26]3[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=3[F:33])[C:5]2=[O:34])[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 7604m-AminoacetanilideHCID 79372,6-LutidineHCID 31374DimethylacetamideHCID 59717263Trifluoromethanesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

生成物 1

HCID 59717354N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide収率 99.2%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
130 °C

実験手順

To trifluoromethanesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 43 (25.0 g) obtained in Step 6 and 3′-aminoacetanilide 57 (7.33 g) were added N,N-dimethylacetamide (50.0 ml) and 2,6-lutidine (5.68 ml), and the mixture was stirred at 130° C. for 5 hrs. After allowing to cool to room temperature, methanol-water [1:2 (volume ratio), 150 ml] was added with stirring. The crystals were collected by filtration and dried to give N-{3-[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]phenyl}acetamide 58 (24.8 g, yield 99%) as colorless crystals.

後処理

  1. temperatureto cool to room temperature
  2. stirringwith stirring
  3. filtrationThe crystals were collected by filtration
  4. customdried

出典と根拠

ORDレコード
ord-8ff25e9cdd494397a1d5b8486d9c5be9
出典データセット
uspto-grants-2014_09
特許番号
US08835443B2

関連ノート

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