Methanol → HCID 68324035, compound

HRID 573619Notes

Reaction equation

HRID 573619 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([C:30]([OH:32])=[O:31])=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:38]O>>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([C:30]([O:32][CH3:38])=[O:31])=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68324148HCID 68324148, compound

Product 1

HCID 68324035HCID 68324035, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]-thieno[2,3-b]pyridine-2-carboxylic acid (90 mg, 0.184 mmol) (Example 35) and concentrated sulfuric acid (0.069 mL, 1.288 mmol) in MeOH (5 mL) was heated at 70° C. under nitrogen for 20 h and then left stand at RT for 2 days. The reaction mixture was then concentrated and purified by chromatography on silica gel, eluting with a gradient of 30-50% ethyl acetate in cyclohexane, to give the title compound (46 mg). LCMS (A) m/z: 503 [M+1]+, Rt 1.41 min (acidic), Rt 0.96 min (basic).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by chromatography on silica gel
  3. washeluting with a gradient of 30-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-9d72f5e1039e4f3e9eb48a0b94b2e22d
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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