Pyridine → [2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

HRID 889376ノート

反応式

HRID 889376 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14]([OH:16])=[O:15])=[C:11]3[CH2:23][CH2:24][CH2:25][C:10]3=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(O[C:37]1[C:42]([F:43])=[C:41]([F:44])[C:40]([F:45])=[C:39]([F:46])[C:38]=1[F:47])=O>CN(C=O)C>[F:43][C:42]1[C:37]([O:15][C:14](=[O:16])[CH:13]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[C:10]3[CH2:25][CH2:24][CH2:23][C:11]=23)[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:38]([F:47])[C:39]([F:46])=[C:40]([F:45])[C:41]=1[F:44]

参加物

5

反応物 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 67387271[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid

生成物 1

HCID 86657983[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid (300 mg, 836 umol) in DMF (3 ml) was added pyridine (70 ul, 920 umol) and pentafluorophenyl trifluoroacetate (290 ul, 1.7 mmol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 12 h, poured onto ice water/0.1 N HCl 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/sat. aqueous NaHCO3 solution 1/1, ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester as an orange oil (762 mg; quant.) which was directly used in the next reaction step without further purification.

後処理

  1. extractionextracted two times with iPrOAc
  2. washThe combined extracts were washed with ice water/
  3. dry with materialaqueous NaHCO3 solution 1/1, ice water/brine 1/1 and dried over Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed under reduced pressure

出典と根拠

ORDレコード
ord-12fb9eab4b68443bab7d68ef2cac214f
出典データセット
uspto-grants-2012_08
特許番号
US08252826B2

反応ノート

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