Hydrochloric Acid → HCID 68612607, compound

HRID 2095370Notes

Reaction equation

HRID 2095370 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[O:25][N:24]=[C:23]([CH2:26][O:27]C3CCCCO3)[CH:22]=2)[CH:20]=1)=O)(C)(C)C.[ClH:34]>CO.CCOCC>[ClH:34].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([C:21]2[O:25][N:24]=[C:23]([CH2:26][OH:27])[CH:22]=2)[CH:18]=[N:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59371644HCID 59371644, compound

Product 1

HCID 68612607HCID 68612607, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-[3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-isoxazolyl]pyridine (145 mg, 0.31 mmol) in MeOH (10 mL) was added at 0° C. 2M anhydrous HCl in ether (10 mL). The reaction mixture was stirred at room temperature for 12 h, then concentrated in vacuo. The residue was purified by HPLC to give the hydrochloride (90 mg). The 1H NMR spectrum (CD3OD, 400 MHz) of this material exhibits signals compatible with the postulated structure, but in addition a second set of signals of somewhat lower intensity for the heteroaromatic protons in close proximity to those of the title compound: δ 9.02 (s, 1H of minor component), 9.01 (s, 1H of major component), 8.74 (narrow m, 1H of minor component), 8.73 (narrow m, 1H of major component), 8.58 (narrow m, 1H of minor component), 8.55 (narrow m, 1H of major component), 7.30 (s, 1H of minor component), 7.28 (s, 1H of major component), 4.74 (s, 2H), 4.71-4.64 (m, 1H), 4.56-4.48 (m, 1H), 4.21-4.32 (m, 1H), 3.49-3.37 (m, 2H), 2.38-2.28 (m, 1H), 2.26-2.06 (m, 2H), 2.04-1.93 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-e6e767fd0d3343b1a24b3067b085f098
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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