Hydrochloric Acid → HCID 59242105, compound

HRID 1876197Notes

Reaction equation

HRID 1876197 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:23])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH2:20][C:21]#[N:22])[N:11]=2)=[CH:5][CH:4]=1.Cl>C(Cl)Cl.CO.[Pd]>[NH2:22][CH2:21][CH2:20][C:12]1[N:11]=[C:10]([N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH3:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59242022HCID 59242022, compound

Product 1

HCID 59242105HCID 59242105, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of {4-[(4-methoxy-phenyl)-methyl-amino]-quinazolin-2-yl}-acetonitrile (250 mg, 0.82 mmol), 10% Pd/C (100 mg) and HCl (12 M, 1 mL, 12 mmol) in CH2Cl2/MeOH (1:1, 10 mL) was treated with H2 (50 psi) and shaken for three days. The Pd/C was filtered off and the filtrate concentrated and purified to give 21 mg of the title compound as a solid. 1H NMR (CDCl3) δ 7.64 (d, 1H), 7.55 (ddd, 1H), 7.13 (d, 2H), 6.95 (m, 2H), 6.93 (d, 2H), 3.85 (s, 3H), 3.62 (t, 2H), 3.56 (s, 3H), 3.4 (t, 2H); LC-MS (ESI+; 309 ([M+H]+)).

Workup

  1. additionwas treated with H2 (50 psi)
  2. filtrationThe Pd/C was filtered off
  3. concentrationthe filtrate concentrated
  4. custompurified

Sources & evidence

ORD record
ord-898538696f564bba8d60ff0f8ae22ebc
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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