Hydrochloric Acid → HCID 86716108, compound

HRID 627546Notes

Reaction equation

HRID 627546 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([O:33]COC)=[CH:29][CH:28]=3)([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[OH:20])[CH:8]=2)[N:3]=1.[ClH:37]>CO>[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([OH:20])([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[CH:8]=2)[N:3]=1.[ClH:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 74222812HCID 74222812, compound

Product 1

HCID 86716108HCID 86716108, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2,4-Dichloro-3-phenylquinolin-6-yl)[4-(methoxymethoxy)phenyl]pyridin-3-ylmethanol (20 mg, 0.039 mmol, Example 23) in MeOH (2 mL) was treated with 37% HCl (1 mL) at room temperature for 18 hours, and concentrated. The residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to give the title compound as an off-white solid. 1H NMR (400 MHz, MeOH-d4) δ 8.85 (d, J=2.20 Hz, 1H), 8.75 (d, J=4.89 Hz, 1H), 8.48 (dt, J=1.80, 8.13 Hz, 1H), 8.31 (d, J=1.96 Hz, 1H), 8.02 (d, J=9.05 Hz, 1H), 7.95 (dd, J=5.62, 8.31 Hz, 1H), 7.86 (dd, J=1.96, 8.80 Hz, 1H), 7.48-7.57 (m, 3H), 7.33 (dd, J=1.47, 7.83 Hz, 2H), 7.08-7.16 (m, 2H), 6.77-6.84 (m, 2H); MS m/e 473.0 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA)

Sources & evidence

ORD record
ord-f2e95e8780ac430b91f88f458a5786b1
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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