Hydrochloric Acid → HCID 59543015, compound

HRID 1045877Notes

Reaction equation

HRID 1045877 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-417622f1a1ee4c7ba8f06e4c8a5187be
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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