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Triethylamine → 1,1-Dimethylethyl (2R,6S)-4-({4-[{[6-(4-fluorophenyl)-2-methyl-3-pyridinyl]carbonyl}(methyl)amino]phenyl}methyl)-2,6-dimethyl-1-piperazinecarboxylate

HRID 534731
ノート
印刷プレビュー

反応式

HRID 534731 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15](Cl)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:18][C@@H:19]1[CH2:24][N:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][CH3:33])=[CH:28][CH:27]=2)[CH2:22][C@H:21]([CH3:34])[N:20]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([N:32]([CH3:33])[C:29]3[CH:28]=[CH:27][C:26]([CH2:25][N:23]4[CH2:24][C@H:19]([CH3:18])[N:20]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:21]([CH3:34])[CH2:22]4)=[CH:31][CH:30]=3)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 592622201,1-Dimethylethyl (2R,6S)-2,6-dimethyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylateHCID 866181086-(4-Fluorophenyl)-2-methyl-3-pyridinecarbonyl chloride

生成物 1

HCID 592621651,1-Dimethylethyl (2R,6S)-4-({4-[{[6-(4-fluorophenyl)-2-methyl-3-pyridinyl]carbonyl}(methyl)amino]phenyl}methyl)-2,6-dimethyl-1-piperazinecarboxylate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

The acid chloride from step 1 was taken up in DCM (3 mL) and added to a solution of 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate (D9) (0.23 g, 0.693 mmol) in DCM (2 mL). Triethylamine (0.193 mL, 1.386 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with DCM and washed with water. The aqueous layer was re-extracted with DCM (×2) and the combined organics were dried and concentrated. The crude product was purified by column chromatography. Elution with 0-50% EtOAc/petroleum yielded the title compound as a white foam (0.331 g). δH (CDCl3, 400 MHz) 7.89 (2H, m), 7.36 (1H, m), 7.26 (1H, m), 7.19 (2H, m), 7.10 (2H, t), 6.99 (2H, m), 4.00 (2H, m), 3.53 (3H, s), 3.34 (2H, s), 2.58 (3H, s), 2.44 (2H, d), 2.05 (2H, m), 1.44 (9H, s), 1.18 (6H, d). MS (ES): MH+ 547.3.

後処理

  1. washwashed with water
  2. extractionThe aqueous layer was re-extracted with DCM (×2)
  3. customthe combined organics were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washElution with 0-50% EtOAc/petroleum

出典と根拠

ORDレコード
ord-fcb11711801e449eaf87dce8ad55f86f
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853218B2

反応ノート

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