Benzhydrylpiperazine → HCID 67359031, compound

HRID 1667188Notes

Reaction equation

HRID 1667188 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[C:10](=[O:18])[CH:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH:25]([N:38]1[CH2:43][CH2:42][N:41]([C:15](=[O:17])[CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH:9]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10]2=[O:18])[CH2:40][CH2:39]1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67358235HCID 67358235, compound

Product 1

HCID 67359031HCID 67359031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-(tert-butoxycarbonyl)-2-oxo-3-phenylpiperazin-1-yl)acetic acid (Example 101C, 0.334 g, 1 mmol) and 1-benzhydrylpiperazine (0.252 g, 1 mmol) in methylene chloride (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.38 g, 1 mmol) and diisopropylethylamine (0.8 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with methylene chloride, and then washed sequentially with 1 N HCl, water, 1 N NaOH, and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.44 (m, 6H), 7.30 (m, 7H), 7.19 (m, 2H), 5.74 (m, 1H), 4.51 (d, J=15.60 Hz, 1H), 4.23 (s, 1H), 4.12 (q, J=7.12 Hz, 1H), 3.96 (d, J=15.94 Hz, 1H), 3.59 (m, 3H), 2.38 (m, 5H), 1.44 (s, 9H); MS (ESI+) m/z 569 (M+H)+.

Workup

  1. washwashed sequentially with 1 N HCl, water, 1 N NaOH, and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9b4b5cee8fd46e2b48901517d5a512f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…