Sodium Cyanide → HCID 59242022, compound

HRID 1876194Notes

Reaction equation

HRID 1876194 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C-:23]#[N:24].[Na+]>CS(C)=O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([CH2:2][C:23]#[N:24])[N:12]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11358914(2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

Product 1

HCID 59242022HCID 59242022, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (50 mg, 0.14 mmol) and NaCN (21 mg, 0.43 mmol) in DMSO was heated by microwave for 10 min at 120° C. The reaction was quenched with H2O, diluted with EtOAc and the layers separated. The aqueous phase was extracted with EtOAc (2×5 mL), washed with brine, filtered over Na2SO4 and concentrated. Purification by gradient MPLC (SiO2, EtOAc/hexanes, 0-50%) gave the desired compound. 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.56 (m, 1H), 7.13 (d, 2H), 7.02 (m, 1H), 6.94 (m, 3H), 4.04 (s, 2H), 3.85 (s, 3H), 3.62 (s, 3H); LC-MS (ESI+; 305 ([M+H]+)) and (ESI−; 303 ([M−H]−)).

Workup

  1. customThe reaction was quenched with H2O
  2. additiondiluted with EtOAc
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with EtOAc (2×5 mL)
  5. washwashed with brine
  6. filtrationfiltered over Na2SO4
  7. concentrationconcentrated
  8. customPurification by gradient MPLC (SiO2, EtOAc/hexanes, 0-50%)

Sources & evidence

ORD record
ord-f0e3c5924e0745dcbfb4deabae59a202
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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