Hydrochloric Acid → {6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid

HRID 532845Notes

Reaction equation

HRID 532845 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][O:6][C:7]1[C:16]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]3[CH:29]=[CH:28][N:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:26]=3)[CH2:19][CH2:18]2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[CH3:36])C.[OH-].[Na+].Cl>C1COCC1>[CH3:36][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]4[CH:29]=[CH:28][N:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:26]=4)[CH2:19][CH2:18]3)[C:7]=1[O:6][CH2:5][C:4]([OH:37])=[O:3])[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59366193{6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl ester

Product 1

HCID 59366173{6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acidYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {6-methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl ester (500 mg, 1.0 mmol) and 2 N NaOH (1 ml, 2 mmol) in THF (3 ml) was stirred at rt for 3 hrs. The solution was then neutralized with 1 N HCl, extracted with mixed solvent (CH2Cl2:iPrOH 80:20) and purified by flash column chromatography on silica gel to give a light yellow solid (300 mg, 64%). MS (ES) m/z 472.2 (M+H+).

Workup

  1. extractionextracted with mixed solvent (CH2Cl2:iPrOH 80:20)
  2. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-5fe6de17695b46bb9f00a355a3eb4a49
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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