Ethyl bromoacetate → 3-[1-(7-Ethoxycarbonylmethoxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

HRID 55049Notes

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].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>>[CH2:39]([O:38][C:36]([CH2:35][O: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])=[O:37])[CH3:40]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 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 229234383-[1-(7-Ethoxycarbonylmethoxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazolineYield 89%

Procedure

The procedure similar to that described in Example 1 was repeated, except that 500.0 mg (1.12 mmol) of Compound 89 obtained in Example 79 was used in place of Compound 24 and ethyl bromoacetate was used in place of methyl iodide. As a result, 530.0 mg (yield: 89%) of Compound 93 was obtained as white crystals.

Sources & evidence

ORD record: ord-c17b6dc3e19941f4860f12a1abbba2b8
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624926

Reaction notes

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