Succinic anhydride → N-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-succinamic acid

HRID 1876209Notes

Reaction equation

HRID 1876209 reaction equation
[NH2:1][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]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1>C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][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][NH:1][C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[N:12]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 44555457(2-Aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

Product 1

HCID 59242125N-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-succinamic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (76 mg, 0.25 mmol) and succinic anhydride (25 mg, 0.25 mmol) was stirred overnight in CH2Cl2 (1 mL). Solvent removal yielded the title compound. 1H NMR (CDCl3) δ 7.80-7.75 (m, 1H), 7.61 (ddd, 1H), 7.23-7.17 (m, 2H), 7.08-6.98 (m, 4H), 4.57 (s, 2H), 3.84 (s, 3H), 3.64 (s, 3H), 2.68-2.62 (m, 4H); HRMS (ES) m/z calcd for C21H23N4O4 395.1714, found 395.1737.

Workup

  1. customSolvent removal

Sources & evidence

ORD record
ord-c4757b38785f47628652d164cb6f2963
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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