Water → 1-{1-[(4-Cyclohexylphenyl)carbonyl]azetidin-3-yl}-4-(phenylcarbonyl)-piperazine

HRID 1911101Notes

Reaction equation

HRID 1911101 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([N:15]3[CH2:18][CH:17]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH2:16]3)=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=N[C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:49]CN(C(C)C)C(C)C.O.CN([CH:62]=[O:63])C>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]([N:15]3[CH2:18][CH:17]([N:19]4[CH2:20][CH2:21][N:22]([C:62]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:49]=5)=[O:63])[CH2:23][CH2:24]4)[CH2:16]3)=[O:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59626057(4-Cyclohexyl-phenyl)-(3-piperazin-1-yl-azetidin-1-yl)-methanone

Product 1

HCID 497631551-{1-[(4-Cyclohexylphenyl)carbonyl]azetidin-3-yl}-4-(phenylcarbonyl)-piperazine

Procedure

To a solution of compound 1j (0.08 g, 0.24 mmol) and HATU (0.093 g, 0.24 mmol) in DMF (3 mL) was added DIPEA (0.1 mL). The mixture was stirred at room temperature for 30 min, and then compound 1k (0.03 g, 0.25 mmol) was added to the mixture. The reaction mixture was stirred at room temperature for 18 h. Water (6 mL) was added to the mixture. The mixture was extracted with EtOAc (2×6 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The crude compound 1 was purified by reverse phase chromatography. 1H NMR (300 MHz, CD3OD): δ 7.58 (d, 2H), 7.44-7.53 (m, 5H), 7.34 (d, 2H), 4.6 (m, 1H), 4.42 (m, 2H), 4.27 (m, 1H), 3.85 (m, 5H), 3.05 (m, 4H), 2.57 (m, 1H), 1.85 (m, 5H), 1.45 (m, 5H). MS m/z (M±H+) 432.3.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. extractionThe mixture was extracted with EtOAc (2×6 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude compound 1 was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-bbf7b9a85e314e54b89c147dd015b0e9
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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