Hydrochloric Acid → HCID 12150102, compound

HRID 1884605Notes

Reaction equation

HRID 1884605 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=[C:28]([NH:36][C:37]([O:39][CH3:40])=[O:38])[C:27]=3[O:41][CH3:42])=[O:24])=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].O.[Li+].[OH-].Cl>CO>[C:32]([C:30]1[CH:29]=[C:28]([NH:36][C:37]([O:39][CH3:40])=[O:38])[C:27]([O:41][CH3:42])=[C:26]([NH:25][C:23](=[O:24])[NH:22][C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([O:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=3)=[CH:13][CH:14]=2)[CH:31]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 12150101HCID 12150101, compound

Product 1

HCID 12150102HCID 12150102, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{4-[3-(5-tert-butyl-2-methoxy-3-methoxycarbonylamino-phenyl)-ureido]-naphthalen-1-yloxy}-pyridine-2-carboxylic acid methyl ester (1.114 g, 2 mmol) in MeOH (12 mL) was added water (2 mL) and LiOH (58 mg, 2.4 mmol). The resulting mixture was stirred at room temperature for 16 h then neutralized with 2N HCl. The resulting suspension was concentrated to dryness and the residual solid triturated with a mixture of methylene chloride and acetonitrile (300 mL, 2:1). The inorganic salt was filtered and the mother liquor concentrated to give the title compound as a dark tan solid (900 mg, 80%).

Workup

  1. concentrationThe resulting suspension was concentrated to dryness
  2. customthe residual solid triturated with a mixture of methylene chloride and acetonitrile (300 mL, 2:1)
  3. filtrationThe inorganic salt was filtered
  4. concentrationthe mother liquor concentrated

Sources & evidence

ORD record
ord-702003d5f2ba4a7d8ecab8b258adb5e4
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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