Hydrochloric Acid → HCID 57906540, compound

HRID 420518Notes

Reaction equation

HRID 420518 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[C:13]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:14][C:9]2=[N:8][CH:7]=1)=[O:5])C.O[Li].O.Cl>CO.O>[C:20]([O:19][C:17]([NH:16][CH2:15][C:13]1[C:12]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:11][N:10]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=[C:9]2[CH:14]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57906583HCID 57906583, compound

Product 1

HCID 57906540HCID 57906540, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 7-(tert-butoxycarbonylamino-methyl)-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (1.39 g, 2.99 mmol) in MeOH (24 mL) and water (12 mL) was added LiOH.H2O (377 mg, 8.98 mmol) in one portion. The slurry was stirred at RT for 14 h then the clear solution was acidified to pH 5 by the addition of 2.0 M HCl in water. The resulting precipitate was filtered, the solid washed with water and dried under vacuum to yield the title compound (1.25 g, 2.76 mmol, 92%) as a colorless solid, which was used in the next step without further purification. MS: 436 [M+1]+; HPLC: AtRet=1.76.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthe solid washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fa7cbfd03755481c95cd1a23281f8997
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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