Hydrochloric Acid → HCID 135448240, compound

HRID 2374902Notes

Reaction equation

HRID 2374902 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:19]2[C:14]([CH:15]=[N:16][C:17]([NH:20][C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)=[N:18]2)=[C:13]([CH3:33])[N:12]=1)(=O)C.C1COCC1.O.[Li+].[OH-].Cl>O.CCOC(C)=O>[CH3:33][C:13]1[N:12]=[C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])[N:19]2[C:14]=1[CH:15]=[N:16][C:17]([NH:20][C:21]1[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=1)=[N:18]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11155130HCID 11155130, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 135448240HCID 135448240, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl acetate (Example 23 below) (26 mg, 0.058 mmol) in 5:1 THF/H2O (4 mL) was added LiOH (30 mg, 1.25 mmol). The reaction was stirred at room temperature for 3 hours then poured into EtOAc (100 mL) and water (20 mL) with aqueous 1 N HCl (2 mL). The aqueous layer was extracted with EtOAc and the combined organic layers then washed with brine, dried over MgSO4, concentrated and purified by silica gel chromatography, eluting with 1% MeOH/DCM to give 2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]-imidazo[5,1-f][1,2,4]triazin-7-yl}phenol (13 mg, (56%)) as a yellow solid. 1H NMR (CDCl3): δ12.73 (s, 1H), 8.94 (dd J=7.87, 1.46 Hz, 1H), 8.86 (s, 1H), 7.31 (m, 1H), 7.09 (d, J=8.06 Hz, 1H), 6.86-6.96 (m, 4H), 3.90 (s, 6H), 3.88 (s, 3H), 2.61 (s, 3H). MS m/z 407 (M+1).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined organic layers then washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 1% MeOH/DCM

Sources & evidence

ORD record
ord-d174403dc9fe4ed3a4da7b23a52c81e2
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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