Chloroform → (1R)-(4-(1-(1-cyclopentyl-3-oxopropyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

HRID 880549ノート

反応式

HRID 880549 の反応式
[CH:1]1(/[CH:6]=[CH:7]/[CH:8]=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.[C:14]([O:20][CH2:21][N:22]1[C:26]2[N:27]=[CH:28][N:29]=[C:30]([C:31]3[CH:32]=[N:33][NH:34][CH:35]=3)[C:25]=2[CH:24]=[CH:23]1)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>[C:14]([O:20][CH2:21][N:22]1[C:26]2[N:27]=[CH:28][N:29]=[C:30]([C:31]3[CH:32]=[N:33][N:34]([C@@H:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][CH:8]=[O:9])[CH:35]=3)[C:25]=2[CH:24]=[CH:23]1)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 6212ChloroformHCID 140680852-Propenal, 3-cyclopentyl-, (2E)-HCID 57868869(4-(1H-Pyrazol-4-yl)-7H-pyrrolo(2,3-d)pyrimidin-7-yl)methyl pivalate

生成物 1

HCID 59420185(1R)-(4-(1-(1-cyclopentyl-3-oxopropyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate収率 80%

試薬・触媒・溶媒 1

HCID 61084-Nitrobenzoic Acid触媒

実験手順

A solution of (2E)-3-cyclopentylacrylaldehyde (28, 345 mg, 2.50 mmol, 5.0 equiv), (2R)-2-bis[3,5-bis(trifluoromethyl)phenyl][(triethylsilyl)oxy]methylpyrrolidine ((R)-35, 16 mg, 0.025 mmol, 0.05 equiv) and 4-nitrobenzoic acid (4.3 mg, 0.025 mmol, 0.05 equiv) in anhydrous chloroform (CHCl3, 2.0 mL, 25 mmol) was stirred at room temperature for 10 min before [4-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate (5, 0.150 g, 0.50 mmol) was added. The resulting reaction mixture was stirred at room temperature for 23 h. After LCMS showed that the reaction was deemed complete, the reaction mixture was concentrated under reduced pressure. The residue was directly purified by Combiflash with 0-80% EtOAc/hexane gradient elution to afford (1R)-(4-(1-(1-cyclopentyl-3-oxopropyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate ((R)-37, 169 mg, 211.8 mg theoretical, 80% yield) as a pale yellow foam. For (R)-37: C23H29N5O3 (MW, 423.51), LCMS (EI) m/e 424 (M++H).

後処理

  1. additionwas added
  2. customThe resulting reaction mixture
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was directly purified by Combiflash with 0-80% EtOAc/hexane gradient elution

出典と根拠

ORDレコード
ord-996cc8b93e7a4e74bf4d08c97adae144
出典データセット
uspto-grants-2015_03
特許番号
US08993582B2

反応ノート

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