Hydrochloric Acid → HCID 68819895, compound

HRID 734349Notes

Reaction equation

HRID 734349 reaction equation
[ClH:1].[CH:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1C=CC2N(O)N=NC=2C=1.Cl>C(Cl)Cl.C(OCC)C.CN(C=O)C.C(Cl)CCl>[ClH:1].[CH:2]([N:5]1[CH2:6][CH2:7][N:8]([C:11]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH:30]4[O:31][CH2:32][CH2:33][NH:28][CH2:29]4)=[O:26])=[CH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:9][CH2:10]1)([CH3:4])[CH3:3]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 68817423HCID 68817423, compound

Product 1

HCID 68819895HCID 68819895, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-isopropyl4-[1-(4-carboxy-phenyl)-piperidin4-carbonyl]-piperazine hydrochloride (D9)(0.25 g), morpholine (0.035 ml), HOBT (0.03 g), TEA (0.16 ml) in DCM (10 ml) was added EDC (0.10 g). DMF (2 ml)was added and the reaction stirred under argon ovemight. The reaction mixture was then evaporated to a minimum and residue dissolved in DCM (50 ml) and washed with sodium hydrogen carbonate (3×50 ml) and then brine (50 ml). The organic layer was then dried (MgSO4) and evaporated to give the free base product. Free base was converted to the HCl salt by dissolving in DCM (5 ml) and treating with excess 1HCl in diethyl ether, evaporated and then crystallised from acetone to give the title compound (E30) as a white solid (0.03 g). MS electrospray (+ve) 429 (MH+). 1H NMR δ [DMSO-d6]: 10.85 (1H, s), 7.38 (2H, d, J=8.4 Hz), 7.08 (2H, m), 4.51 (1H, m), 4.22 (1H, m), 3.81 (2H, m), 3.68-3.35 (12H, m), 3.20-2.81 (6H, m), 1.74 (4H, m), 1.29 (6H, d, J=6.4 Hz).

Workup

  1. customThe reaction mixture was then evaporated to a minimum and residue
  2. dissolutiondissolved in DCM (50 ml)
  3. washwashed with sodium hydrogen carbonate (3×50 ml)
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. customevaporated
  6. customto give the free base product
  7. customevaporated
  8. customcrystallised from acetone

Sources & evidence

ORD record
ord-9b3dd56d03484e2d83e25db6d4e63ed8
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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