Hydrochloric Acid → HCID 18542191, compound

HRID 396539Notes

Reaction equation

HRID 396539 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[S:21][N:20]=[N:19][C:18]=1[CH3:22])=[O:16].Cl>C(O)(=O)C>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:15]([C:17]1[S:21][N:20]=[N:19][C:18]=1[CH3:22])=[O:16])=[C:5]2[CH2:4][C:3]([OH:23])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23003614HCID 23003614, compound

Product 1

HCID 18542191HCID 18542191, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl[5-chloro-2-(4-methyl-1,2,3-thiadiazole-5-carbonyl)-1H-indol-3-yl]acetate (Example 228, 190 mg, 0.54 mmol), 2N aqueous HCl (4 ml), and acetic acid (20 ml) was heated at reflux temperature for 2 h. After cooling to room temperature, the mixture was concentrated. The crystalline residue was diluted with THF (100 ml) and dried (MgSO4) and concentrated. The residual solids were washed with ethyl acetate gave 145 mg (79%) of the title compound as yellow solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. concentrationthe mixture was concentrated
  4. additionThe crystalline residue was diluted with THF (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washThe residual solids were washed with ethyl acetate

Sources & evidence

ORD record
ord-b482a467798b44a18880033cb11abcc0
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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