Hydrochloric Acid → HCID 136124375, compound

HRID 2224950Notes

Reaction equation

HRID 2224950 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:17])([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:35])(=[O:34])[N:20]=1.Cl.[O:37]1CCOCC1>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]([OH:37])([CH3:15])[CH3:16])([CH3:17])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:35])(=[O:34])[N:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 136124365HCID 136124365, compound

Product 1

HCID 136124375HCID 136124375, compound

Procedure

To a solution of Example 139 (40 mg, 0.078 mmol) in dioxane (3 mL) was added a solution of 6N aqueous hydrochloric acid (3 mL). The mixture was heated at 65 C for 3 hours, and the solvent removed in vacuo. The resultant residue was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% trifluoroacetic acid in water over 8 minutes (10 minutes run time) at a flow rate of 40 mL/min to provide the title (6 mg, 14%). MS (ESI) m/z=532 (M−H)+. 1H NMR (500 MHz, DMSO-d6): δ 0.60 (dq, J=12.8, 3.7 Hz, 1H), 0.91 (s, 6H), 0.98 (dq, J=12.8, 4.3 Hz, 1H), 1.59 (s, 3H), 2.09 (m, 1H), 2.26 (dq, J=12.8, 4.3 Hz, 1H), 3.07 (s, 3H), 7.56 (m, 3H), 7.74 (m, 3H), 8.16 (d, J=7.9 Hz, 1H), 10.22 (s, 1H), 13.77 (s, 1H).

Workup

  1. temperatureThe mixture was heated at 65 C for 3 hours
  2. customthe solvent removed in vacuo
  3. customThe resultant residue was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  4. customover 8 minutes
  5. custom(10 minutes run time)
  6. customto provide the title (6 mg, 14%)

Sources & evidence

ORD record
ord-eff18adf8c1f45cf98fb1d4c463316c0
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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