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Acetic Anhydride → N-acetyl-N-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-acetamide

HRID 1517079
ノート
印刷プレビュー

反応式

HRID 1517079 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.CCN([CH2:37][CH3:38])CC.[C:39](OC(=O)C)(=[O:41])[CH3:40].C(=O)([O-])[O-:47].[Na+].[Na+]>CC(C)=O>[CH3:21][C:5]1[CH:4]=[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:2]([NH:1][C:39](=[O:41])[CH3:40])=[N:7][C:6]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:12][CH2:11]1)=[O:9].[C:39]([N:1]([C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[CH:4][C:5]([CH3:21])=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:12][CH2:11]2)=[O:9])[N:7]=1)[C:37](=[O:47])[CH3:38])(=[O:41])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 44547360[6-Amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

生成物 2

HCID 57441146N-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-acetamide
HCID 58016733
N-acetyl-N-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-acetamide
収率 37%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 0.22 g (0.5 mmol) of [6-amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 7) in 5 ml of acetone was treated with 0.35 ml=0.26 g (2.5 mmol) of Et3N, followed by 0.19 ml=0.21 g (2.0 mmol) of acetic anhydride and the reaction mixture was subsequently heated up to reflux. After 22 hours, it was poured into crashed ice, the pH was adjusted to 8-9 with sodium carbonate solution and it was extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 3:2) to give 0.12 g (51%) the N-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-acetamide as light yellow solid [MS: 475.2 (MH+)] and 0.098 g (37%) of N-acetyl-N-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-acetamide as yellow solid. MS: 517.2 (MH+).

後処理

  1. temperaturethe reaction mixture was subsequently heated up
  2. temperatureto reflux
  3. additionit was poured
  4. extractionwas extracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 3:2)

出典と根拠

ORDレコード
ord-f81965d9ded34299a3923957732c3859
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227613B2

反応ノート

読み込み中…

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