Water → HCID 59277719, compound

HRID 1097787Notes

Reaction equation

HRID 1097787 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[N:12]([CH:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19](C(=O)C3C=CC=CC=3)[CH2:18][C:17]2([CH3:35])[CH3:34])[CH:13]=[N:14][CH:15]=1)=O.[F-].[Na+].O>C1COCC1>[CH3:34][C:17]1([CH3:35])[CH:16]([N:12]2[C:11]([CH2:9][OH:8])=[CH:15][N:14]=[CH:13]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 24957696HCID 24957696, compound

Product 1

HCID 59277719HCID 59277719, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (26 mg, 0.68 mmol) is carefully added to a solution of 3-(1-benzoyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (101 mg, 0.26 mmol) in THF (10 mL) at 0° C. The resulting mixture is warmed up to room temperature. After overnight, NaF and water are added at 0° C. Then the reaction mixture is warmed up to room temperature and stirred until the grey suspension turned to off white color. The mixture is filtered and the filtrate is concentrated and taken up into ethyl acetate and washed with brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by flash chromatography and gives the title compound (23 mg, 34.5% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.81 (s, 3 H), 1.08 (s, 3 H), 2.68 (br. s., 1 H), 2.97 (d, J=12.1 Hz, 1 H), 3.19 (d, J=12.1 Hz, 1 H), 4.22 (br. s., 1 H), 4.73 (s, 2 H), 5.11 (s, 1 H), 6.54-6.61 (m, 2 H), 6.87 (s, 1 H), 6.92 (d, J=7.3 Hz, 1 H), 7.08 (t, J=8.3 Hz, 1 H), 7.28 (s, 1 H). HRMS: calculated for C15H20N3O: 258.1606. Found: 258.1615.

Workup

  1. temperatureThen the reaction mixture is warmed up to room temperature
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration
  7. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-9eea722b849f498bbf08c2b07fae5881
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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