HCID 68516416, compound → HCID 59242015, compound

HRID 1876198Notes

Reaction equation

HRID 1876198 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[N:14]=[C:13]([N:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:25])[CH:11]=2)[N:6]=1.NCC1N=C(N(C2C=CC(OC)=CC=2)C)C2C(=CC=C([N+]([O-])=O)C=2)N=1>CC(O)=O.[Pd]>[NH2:3][CH2:4][C:5]1[N:14]=[C:13]([N:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:25])[CH:11]=2)[N:6]=1

Participants

5

Reactant 2

HCID 68516416HCID 68516416, compoundHCID 68519277HCID 68519277, compound

Product 1

HCID 59242015HCID 59242015, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-Aminomethyl-N4-(4-methoxyphenyl)-N4-methylquinazoline-4,6-diamine bis(hydrochloride): (2-Aminomethyl-6-nitro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (120 mg, 0.35 mmol) was hydrogenated over 10% Pd/C in AcOH (5 mL) for 1 h. The suspension was filtered through Celite, washing with MeOH, and concentrated. The residue was suspended in CH2Cl2 and treated with Na2CO3. The mixture was then concentrated onto Celite and purified by gradient MPLC (amine column, MeOH/CH2Cl2, 0-100%). The residue was suspended in H2O and treated with excess 2 N HCl and lypholized, yielding 69.0 mg (52%) of the title compound. 1H NMR (DMSO-d6) δ 7.86 (d, 1H), 7.78 (dd, 1H), 7.42-7.50 (m, 2H), 7.12-7.20 (m, 2H), 6.74 (d, 1H), 4.62 (s, 2H), 3.93 (s, 3H), 3.92 (s, 3H); HRMS (ES) m/z calcd for C17H20N5O (M+H) 310.1662, found 310.1691.

Workup

  1. filtrationThe suspension was filtered through Celite
  2. washwashing with MeOH
  3. concentrationconcentrated
  4. additiontreated with Na2CO3
  5. concentrationThe mixture was then concentrated onto Celite
  6. custompurified by gradient MPLC (amine column, MeOH/CH2Cl2, 0-100%)
  7. additiontreated with excess 2 N HCl

Sources & evidence

ORD record
ord-92af9c01e51a4ba1833ad258ddceb03d
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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