Dichloromethane → (E)-3-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride

HRID 1711848ノート

反応式

HRID 1711848 の反応式
C([O:5][C:6](=[O:23])[CH:7]=[CH:8][C:9]1[CH:10]=[N:11][C:12]([NH2:22])=[C:13]([CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:32]>>[ClH:32].[NH2:22][C:12]1[N:11]=[CH:10][C:9](/[CH:8]=[CH:7]/[C:6]([OH:23])=[O:5])=[CH:14][C:13]=1[CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 669669103-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid tert-butyl ester

生成物 1

HCID 66966962(E)-3-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride

実験手順

A suspension of 3-(6-amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid tert-butyl ester (250 mg, 0.79 mmol) in CH2Cl2 (3 mL) was treated with TFA (2 mL). After stirring at room temperature under N2 for 45 min, the solution was concentrated. The resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M) and then sonicated until the oil was converted to a fine off-white solid. After stirring under N2 for 20 min, the solid was isolated by filtration, washed with Et2O, and dried under vacuum for several hours to give the title compound (282 mg, quantitative) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.6 (br s, 1H), 8.53 (d, J=2.1 Hz, 1H), 8.39-8.28 (m, 3H), 7.53 (d, J=15.0 Hz, 1H), 6.46 (d, J=15.0 Hz, 1H), 4.33 (s, 2H), 3.43-3.35 (m, 2H), 2.97 (s, 2H), 1.79-1.69 (m, 5H), 1.35 (s, 1H).

後処理

  1. concentrationthe solution was concentrated
  2. additionThe resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M)
  3. customsonicated until the oil
  4. stirringAfter stirring under N2 for 20 min
  5. customthe solid was isolated by filtration
  6. washwashed with Et2O
  7. customdried under vacuum for several hours

出典と根拠

ORDレコード
ord-e9005324574a44da8cdaa4d8cf99cbe0
出典データセット
uspto-grants-2010_09
特許番号
US07790709B2

反応ノート

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