1-Iodopropane → 1,2,3,4-Tetrahydro-3-[1-(6-methoxy-7-propoxy-4-quinazolinyl)-4-piperidinyl]-1,6-dimethyl-2,4-dioxo-quinazoline

HRID 2257743Notes

Reaction equation

HRID 2257743 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([CH3:29])[CH:25]=5)[N:20]([CH3:30])[C:19]4=[O:31])[CH2:14][CH2:13]3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:32][CH3:33].[CH2:34](I)[CH2:35][CH3:36]>>[CH3:33][O:32][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:34][CH2:35][CH3:36])[N:9]=[CH:8][N:7]=[C:6]2[N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:29])[CH:25]=3)[N:20]([CH3:30])[C:19]2=[O:31])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 336431-IodopropaneHCID 1358475911,2,3,4-Tetrahydro-3-[1-(7-hydroxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,6-dimethyl-2,4-dioxo-quinazoline

Product 1

HCID 229234031,2,3,4-Tetrahydro-3-[1-(6-methoxy-7-propoxy-4-quinazolinyl)-4-piperidinyl]-1,6-dimethyl-2,4-dioxo-quinazoline

Procedure

The procedure similar to that described in Example 1 was repeated, except that 223.5 mg (0.50 mmol) of Compound 89 obtained in Example 79 was used in place of Compound 24 and propyl iodide was used in place of methyl iodide. As a result, a free base of Compound 91 was obtained, which was then converted to the hydrochloride in the similar manner as in Example 41 to give 229.9 mg (yield: 87%) of the hydrochloride of Compound 91 as white crystals.

Sources & evidence

ORD record
ord-3c53da10c0414d03826eb5433bd31c48
Source dataset
uspto-grants-1997_08
Patent number
US05658917

Reaction notes

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