HCID 67539565, compound → HCID 67539710, compound

HRID 1192380Notes

Reaction equation

HRID 1192380 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C>C(Cl)Cl.Cl.CCOCC>[ClH:33].[ClH:33].[NH2:7][C@H:8]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 1

HCID 67539565HCID 67539565, compound

Product 1

HCID 67539710HCID 67539710, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-[1-(4-chlorobenzyl)-2-(4-imidazo[1,2-a]pyridin-3-yl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (350 mg, 0.72 mmol) in DCM (3 mL) and 2.0N HCl in Et2O (2 mL) was stirred for 12 hours. The mixture was concentrated in vacuo and the resulting material was chromatographed (SiO2) using 10% MeOH/DCM followed by 10% (7N NH3 in MeOH)/DCM as eluent. This material was dissolved in MeOH followed by the addition of 2.0N HCl in Et2O, and then concentrated in vacuo. The resulting gum was tripped from isopropyl alcohol, and then from acetonitrile to give 2-(R)-amino-3-(4-chlorophenyl)-1-(4-imidazo[1,2-a]pyridin-3-yl-piperazin-1-yl)-propan-1-one dihydrochloride as a white solid (100 mg). 1H NMR (DMSO-d6, 400 MHz) δ 8.66 (d, J=6.8 Hz, 1H), 8.49 (bs, 3H), 7.89 (m, 3H), 7.45 (m, 1H), 7.38 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H), 4.69 (bs, 1H), 3.49 (m, 6H), 3.08 (m, 1H), 2.94 (m, 3H), 2.85 (m, 1H). LCMS (APCI+) m/z 384, 386 [m+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting material was chromatographed (SiO2)
  3. dissolutionThis material was dissolved in MeOH
  4. additionfollowed by the addition of 2.0N HCl in Et2O
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dafe0714803d490db131f6c7e4a320a5
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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