Hexafluoroacetylacetone → 2-[4,6-Bis(trifluoromethyl)pyrimidin-2-yl]-5-{[2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

HRID 244031ノート

反応式

HRID 244031 の反応式
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]2[N:32]=[CH:31][CH:30]=[N:29]2)[C:10]=1[C:11]([N:13]1[CH2:17][CH:16]2[CH2:18][N:19]([C:21](=[NH:23])[NH2:22])[CH2:20][CH:15]2[CH2:14]1)=[O:12].C[O-].[Na+].[F:36][C:37]([F:48])([F:47])[C:38](=O)[CH2:39][C:40](=O)[C:41]([F:44])([F:43])[F:42]>C(O)CCC>[F:36][C:37]([F:47])([F:48])[C:38]1[CH:39]=[C:40]([C:41]([F:42])([F:43])[F:44])[N:22]=[C:21]([N:19]2[CH2:18][CH:16]3[CH:15]([CH2:14][N:13]([C:11]([C:10]4[C:24]([N:28]5[N:32]=[CH:31][CH:30]=[N:29]5)=[CH:25][CH:26]=[CH:27][C:9]=4[F:8])=[O:12])[CH2:17]3)[CH2:20]2)[N:23]=1

参加物

5

反応物 3

HCID 73706HexafluoroacetylacetoneHCID 10942334Sodium MethoxideHCID 866691735-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydro-pyrrolo[3,4-c]pyrrole-2(1H)-carboximidamide TFA salt

生成物 1

HCID 849729832-[4,6-Bis(trifluoromethyl)pyrimidin-2-yl]-5-{[2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole収率 6.2%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

Crude 5-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydro-pyrrolo[3,4-c]pyrrole-2(1H)-carboximidamide—TFA salt (66 mg) was diluted with n-butanol (4 mL) and treated with sodium methoxide (51.9 mg, 0.961 mmol). The reaction is heated to reflux for 1 hour, then cooled and 1,1,1,5,5,5-hexafluoropentane-2,4-dione (400 mg, 1.92 mmol) is added prior to re-heating the reaction to reflux for 19 hours. The mixture was then cooled and concentrated, then diluted with DCM and saturated sodium bicarbonate. Extract with DCM and concentrate. Reverse phase HPLC gave the title compound (4.6 mg). MS (ESI): mass calculated for C21H16F7N7O, 515.39; m/z found 416.2 [M+H]+. Rotamers observed in 1H NMR.

後処理

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. temperatureto re-heating
  5. customthe reaction
  6. temperatureto reflux for 19 hours
  7. temperatureThe mixture was then cooled
  8. concentrationconcentrated
  9. additiondiluted with DCM and saturated sodium bicarbonate
  10. extractionExtract with DCM
  11. concentrationconcentrate

出典と根拠

ORDレコード
ord-07bf3e8fd9db4b8ead0e90368f7d35b3
出典データセット
uspto-grants-2014_02
特許番号
US08653263B2

反応ノート

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