Hydrochloric Acid → HCID 59367639, compound

HRID 2079828Notes

Reaction equation

HRID 2079828 reaction equation
C(OC([O:8][NH:9][C:10](=[O:35])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH:21]3[CH:19]([CH:20]3[NH:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)[CH2:18]2)=[CH:13][CH:12]=1)C)C(C)C.Cl>C(Cl)Cl.O1CCOCC1>[OH:8][NH:9][C:10](=[O:35])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH:21]3[CH:19]([CH:20]3[NH:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)[CH2:18]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59367666HCID 59367666, compound

Product 1

HCID 59367639HCID 59367639, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(1-Isobutoxyethoxy) 4-{6-[(naphthalen-2-ylmethyl)-amino]-3-aza-bicyclo[3.1.0]hex-3-yl}-benzamide (117 mg, 0.25 mmol) was stirred in DCM (10 ml) at r.t. and 4M HCl in dioxane (0.5 ml) was added. The reaction was allowed to stir for 30 min and then the solvent was removed in vacuo. The residue was purified by Gilson HPLC to give the title compound as a pink solid (13 mg, 14%). LCMS purity 98%, m/z 374 [M+H]+. 1H NMR (300 MHz, CD3OD) δ: 2.25 (2H, br s), 2.71 (1H, s), 3.32 (2H, m), 3.71 (2H, d, J=9.3 Hz), 4.54 (2H, s), 6.61 (2H, d, J=8.1 Hz), 7.62 (5H, m), 7.95 (4H, m), no peaks for NH/NHOH due to CD3OD.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by Gilson HPLC

Sources & evidence

ORD record
ord-70a6d3e223a147bfb65499d5ef57b335
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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