2-Pyrrolidone → HCID 59242086, compound

HRID 1876229Notes

Reaction equation

HRID 1876229 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.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C([Li])CCC.COC1C=CC(CNC2C3C(=CC=CC=3)N=C(CN3CCCCC3=O)N=2)=CC=1>C1COCC1>[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][N:23]3[CH2:27][CH2:26][CH2:25][C:24]3=[O:28])[N:12]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 120252-PyrrolidoneHCID 11358914(2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amineHCID 68518044HCID 68518044, compoundHCID 178418339Butyllithium

Product 1

HCID 59242086HCID 59242086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (150 mg, 0.43 mmol), 2-pyrrolidinone (128 mg, 1.5 mmol) and n-butyllithium (2.5 M in THF, 1.2 mL, 3 mmol) in THF (2 mL) by a procedure similar to the preparation of 1-{4-[(4-methoxyphenyl)methylamino]quinazolin-2-ylmethyl}piperidin-2-one in Example 252 and was isolated as a yellow solid. 1H NMR (CDCl3) δ 7.75-7.73 (m, 1H), 7.55-7.51 (m, 1H), 7.13-7.10 (d, 2H), 6.99-6.97 (m, 2H), 6.93-6.90 (d, 2H), 4.72 (s, 2H), 3.84 (s, 3H), 3.61 (t, 2H), 3.54 (s, 3H), 2.53 (t, 2H), 2.15-2.10 (pentet, 2H); LC-MS (ESI+; 363 ([M+H]+)).

Workup

  1. customwas isolated as a yellow solid

Sources & evidence

ORD record
ord-a89fba2e19924f348ae59deda7a0156f
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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