Borane → HCID 59199430, compound

HRID 2089525Notes

Reaction equation

HRID 2089525 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]([CH3:20])[C:11]2=O)[CH:7]=[N:8][CH:9]=1)=[O:4].B.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]([CH3:20])[CH2:11]2)[CH:7]=[N:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6331BoraneHCID 14798Sodium HydroxideHCID 59199422HCID 59199422, compound

Product 1

HCID 59199430HCID 59199430, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(2-methyl-3-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (90 mg, 0.316 mmol) in THF (2 mL) is added a 1 M solution of borane in THF (1.6 mL, 1.6 mmol). The reaction is permitted to stir for 1 hour, at which time it is quenched with 1 M aqueous HCl. The acidified reaction is permitted to stir for one hour and then is treated with 1 N aqueous NaOH until the pH is >7. The mixture is then extracted with dichloromethane. The organic extract is dried over Na2SO4, filtered, and concentrated. The resulting residue is purified by semi-preparative reverse phase HPLC (5 to 100% acetonitrile/water w/0.1% NH4OH) to furnish 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 272.2 (M+H)+. The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCl salt of 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; 1H NMR (400 MHz, CDCl3) δ ppm 2.39 (s, 3 H), 2.80 (dd, J=12.4, 3.8 Hz, 1 H), 2.94-3.02 (m, 1 H), 3.40 (d, J=15.2 Hz, 1 H), 3.91 (s, 3 H), 3.90-3.96 (m, 1 H), 6.35 (m, 1 H), 7.11-7.23 (m, 3 H), 7.24-7.32 (m, 1 H), 7.50 (s, 1 H), 7.77 (s, 1 H).

Workup

  1. customis quenched with 1 M aqueous HCl
  2. customThe acidified reaction
  3. stirringto stir for one hour
  4. extractionThe mixture is then extracted with dichloromethane
  5. extractionThe organic extract
  6. dry with materialis dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by semi-preparative reverse phase HPLC (5 to 100% acetonitrile/water w/0.1% NH4OH)

Sources & evidence

ORD record
ord-01983b91f3394aa0b7e04b82bec62ba0
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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