Tetrahydrofuran → HCID 135430303, compound

HRID 2258435Notes

Reaction equation

C(N(CC)CC)C.NCCCN1C=CN=C1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([NH:31][CH2:32][CH3:33])=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1.[O:34]1CCCC1>>[CH2:32]([NH:31][C:24]1[CH:23]=[C:22]2[C:27]([C:18](=[O:34])[NH:19][CH:20]=[N:21]2)=[CH:26][C:25]=1[N+:28]([O-:30])=[O:29])[CH3:33]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 787361H-Imidazole-1-propanamine

HCID 232929894-Chloro-7-ethylamino-6-nitroquinazoline

Product 1

HCID 135430303HCID 135430303, compound

Procedure

Triethylamine (10 ml, 71.7 mmol) and 1-(3-aminopropyl)imidazole (5 ml, 41.9 mmol) were added to a tetrahydrofuran solution (10 ml) of 4-chloro-7--ethylamino-6-nitroquinazoline obtained from 7-ethylamino-6-nitro-4(3H)-quinazolone (610.3 mg, 2.61 mmol) in Reference Example 13 under ice-cooling. The mixture was stirred at room temperature for 19 hours and at 50° C. for 12 hours. After the solvent was distilled off, the residue was purified by silica gel column chromatography (elution with chloroform:methanol=30:1) to give Solid A (800 mg, 89.9%).

Sources & evidence

ORD record: ord-23aa5733ca0247a583fddcb1c68788eb
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661147

Reaction notes

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