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 55047Notes

Reaction equation

HRID 55047 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-d0bd61e0c99a460fb2e45e322b27cd86
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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