Hydrochloric Acid → 4-[7-(1-Quinolin-6-ylcyclopropyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoic acid

HRID 500220Notes

Reaction equation

HRID 500220 reaction equation
O.[OH-].[Li+].[N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3([C:17]4[N:21]5[N:22]=[C:23]([C:26]6[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=6)[CH:24]=[N:25][C:20]5=[N:19][CH:18]=4)[CH2:16][CH2:15]3)=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.O.Cl>C1COCC1.CO>[N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3([C:17]4[N:21]5[N:22]=[C:23]([C:26]6[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=6)[CH:24]=[N:25][C:20]5=[N:19][CH:18]=4)[CH2:15][CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67224613Methyl 4-[7-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate

Product 1

HCID 672247994-[7-(1-Quinolin-6-ylcyclopropyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (14 mg, 0.34 mmol) was added to a solution of methyl 4-[7-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate (30.0 mg, 0.07 mmol) in THF (0.3 mL), methanol (0.3 mL), and water (0.2 mL). The mixture was stirred at RT for 2 h and adjusted to pH 2 with conc. HCl. The volatiles were removed under reduced pressure and the residue was dried to provide the crude product which was directly used in the next step without further purification. LCMS: (M+H)=408.1.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was dried

Sources & evidence

ORD record
ord-0b3ee925e6524ac799cc4d3fdf0290c0
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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