Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 2-[1-(4-Acetyl-phenyl)-piperidin-4-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

HRID 2262707ノート

反応式

HRID 2262707 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:20]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:24][CH2:23][CH2:22]C1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][C:17]([N:28]3[CH2:27][CH2:26][N:25]([CH:20]4[CH2:22][CH2:23][CH2:24]4)[CH2:30][CH2:29]3)=[O:19])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 8064211-CyclopentylpiperazineHCID 49759600[1-(4-Acetyl-phenyl)-piperidin-4-YL]-acetic acid

生成物 1

HCID 574424042-[1-(4-Acetyl-phenyl)-piperidin-4-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [1-(4-acetyl-phenyl)-piperidin-4-yl]-acetic acid (0.11 mmol) in anhydrous DCM (2 mL) is added 1-cyclopentylpiperazine (1.1 eq.), TEA (0.22 mmol), and BOP (0.14 mmol). The resulting mixture is stirred at rt overnight. DCM is evaporated. The residue is dissolved in EtOAc (20 mL), washed with water (5 mL×3) and brine, dried over sodium sulfate, and concentrated. The crude product is purified through PTLC to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.85 (2H, d), 6.85 (2H, d), 3.89 (2H, br), 3.66 (2H, t), 3.49 (2H, t), 2.91 (2H, dt), 2.46˜2.57 (8H, overlapped), 2.26 (2H, d), 2.12 (1H, m), 1.22˜1.95 (12H, m); LC-MS (M+1) 398.

後処理

  1. customDCM is evaporated
  2. dissolutionThe residue is dissolved in EtOAc (20 mL)
  3. washwashed with water (5 mL×3) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified through PTLC

出典と根拠

ORDレコード
ord-560002b7921b493fa74d17edcb3fa32d
出典データセット
uspto-grants-2010_12
特許番号
US07851474B2

反応ノート

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