Ethylamine → HCID 24805173, compound

HRID 1690736Notes

Reaction equation

HRID 1690736 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:11]([N:12]2[C:16]([CH:17]=O)=[CH:15][N:14]=[CH:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:19])[O:3]1.[CH2:21]([NH2:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:21]([NH:23][CH2:17][C:16]1[N:12]([CH:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:19])[O:3][C:2]2([CH3:20])[CH3:1])[CH:13]=[N:14][CH:15]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 248026903-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde

Product 1

HCID 24805173HCID 24805173, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde (0.133 g, 0.49 mmol) (Example 9a) in dichloroethane (2 mL) is added ethylamine (0.37 mL, 0.738 mmol) and sodium triacetoxyborohydride (0.313 g, 1.477 mmol). The reaction mixture is stirred at 50° C. for 5 h. The mixture is cooled to room temperature, washed with saturated aqueous sodium bicarbonate and is extracted with ethyl acetate. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is dissolved in methanol (5 mL) and purified by reverse phase HPLC to give 4-(5-ethylaminomethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one; HRMS (ESI) m/z 300.1705 [(M+H)+: Calcd for C17H22N3O2: 300.1712]; 1H NMR (400 MHz, MeOD) of the TFA salt δ ppm 1.27 (s, 3 H), 1.46 (t, J=6.8 Hz, 3 H), 1.59 (s, 3 H), 3.35-3.40 (m, 2 H), 4.65 (br. s, 2 H), 5.82 (s, 1 H), 7.51 (br. s, 1 H), 7.64 (d, J=7.3 Hz, 1 H), 7.75 (td, J=7.8, 1.0 Hz, 1 H), 7.84 (td, J=7.6, 1.3 Hz, 1 H), 7.92 (br. s, 1 H), 8.30 (dd, J=7.8, 1.3 Hz, 1 H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. extractionis extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in methanol (5 mL)
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-8662a6688a664ecf98bcea855c644488
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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