Hydrochloric Acid → HCID 59543015, compound

HRID 336486Notes

Reaction equation

HRID 336486 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C@@H:6]1[CH2:10][S:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[NH:21][CH:22]2[CH2:31][CH2:30][C:25]3(OCC[O:26]3)[CH2:24][CH2:23]2)=[N:7]1)C.Cl>CO>[CH3:20][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([NH:21][CH:22]3[CH2:31][CH2:30][C:25](=[O:26])[CH2:24][CH2:23]3)[CH:15]=1)[NH:12][C:11]([C:8]1[S:9][CH2:10][C@@H:6]([CH2:5][C:4]([OH:32])=[O:3])[N:7]=1)=[CH:19]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68486748HCID 68486748, compound

Product 1

HCID 59543015HCID 59543015, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{(R)-2-[7-(1,4-dioxa-spiro[4,5]dec-8-yl)amino-5-methyl-1H-indol-2-yl]-4,5-dihydro-thiazol-4-yl}-acetic acid ethyl ester (177 mg, 4 mmol) prepared in Step A was dissolved in methanol (10 mL). HCl (conc. 2 mL) was added thereto, and the mixture was reacted for 6 h at 60° C. The solvent was removed under reduced pressure, and water was added to the residue. The reaction mixture was extracted with EtOAc, dried, concentrated, and purified by HPLC to give the title compound (76 mg, Yield 50%).

Workup

  1. customthe mixture was reacted for 6 h at 60° C
  2. customThe solvent was removed under reduced pressure, and water
  3. additionwas added to the residue
  4. extractionThe reaction mixture was extracted with EtOAc
  5. customdried
  6. concentrationconcentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-27ce7952b4504ddb9ab4906365d918c6
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

Loading…