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

HRID 2262707노트

반응식

HRID 2262707 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-560002b7921b493fa74d17edcb3fa32d
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851474B2

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