Hydrochloride methanol → HCID 71523146, compound

HRID 1621003Notes

Reaction equation

HRID 1621003 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:22]([OH:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CO>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[OH:29])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 89524677HCID 89524677, compound

Product 1

HCID 71523146HCID 71523146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 140C (390 mg, 0.866 mmol) in MeOH (2 mL) was added HCl/MeOH (2 M, 2 mL, 4 mmol) at room temperature. The reaction mixture was stirred at ambient temperature overnight. The solvent was removed in vacuo. The resulting residue was partitioned between EtOAc (20 mL) and saturated NaHCO3 (20 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated. Crude product was purified by Prep-HPLC (Column: Waters X-bridge ODS C18 21.2×250 mm, water (0.05% TFA): acetonitrile 45-85%) to give Example 140D. LCMS: 450[M+1]. 1H NMR (400 MHz, DMSO-d6): δ 12.81 (s, 1H), 7.76 (s, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.37-7.46 (m, 3H), 7.20 (d, J=16.0 Hz, 1H), 2.61 (s, 3H), 2.37 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe resulting residue was partitioned between EtOAc (20 mL) and saturated NaHCO3 (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrude product was purified by Prep-HPLC (Column: Waters X-bridge ODS C18 21.2×250 mm, water (0.05% TFA): acetonitrile 45-85%)
  8. customto give Example 140D

Sources & evidence

ORD record
ord-c3b1788e62024dbdae5a45f43c0d98be
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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