Putrescine → HCID 59242092, compound

HRID 1876181Notes

Reaction equation

HRID 1876181 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[CH2:31]([NH2:36])[CH2:32][CH2:33][CH2:34][NH2:35]>C(O)CCC>[NH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:36][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1045PutrescineHCID 81531DiisopropylethylamineHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 59242092HCID 59242092, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (300 mg, 1.0 mmol) in n-butanol (3 mL) and diisopropylethylamine (323 mg, 2.5 mmol) was added 1,4-butanediamine (132 mg, 1.5 mmol). The reaction was heated to 105° C. for 18 h, cooled to room temperature and concentrated. The crude product was purified by chromatography (amine column, i-PrOH/CHCl3, 0-100%) to give 138 mg (39%) of the title compound. 1H NMR (CDCl3) δ 7.5 (d, 1H), 7.4 (t, 1H), 7.15 (d, 2H), 6.95 (d, 2H), 6.7 (m, 2H), 3.8 (s, 3H), 3.6 (s, 3H), 3.55 (t, 2H), 2.8 (t, 2H), 2.1 (s, 3H), 1.75 (pentet, 2H), 1.63 (pentet, 2H); LC-MS (ESI+; 352 ([M+H]+)).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography (amine column, i-PrOH/CHCl3, 0-100%)

Sources & evidence

ORD record
ord-4b50e8510a874e9abfc5b709ba2b68c5
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…