Methyl 3-(bromomethyl)benzoate → 1-(3-(4-(Cyclohexylcarbonyl)piperazine-1-carbonyl)benzyl)-8-fluoroquinazoline-2,4(1H,3H)-dione

HRID 927300Notes

Reaction equation

HRID 927300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](O)=[O:20])[CH:14]=1)[C:7](=[O:22])[NH:6][C:5]2=[O:23].F[C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)N[C:30](=O)[NH:29][C:28]2=[O:36].BrCC1C=C(C=CC=1)C(OC)=O.COC(C1C=[C:55](C=CC=1)[CH2:56][N:57]1C2C(=CC=CC=2)C(=O)N[C:58]1=O)=O>>[CH:27]1([C:28]([N:29]2[CH2:55][CH2:56][N:57]([C:19]([C:15]3[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=3)[CH2:12][N:8]3[C:3]4[C:4](=[CH:9][CH:10]=[CH:11][C:2]=4[F:1])[C:5](=[O:23])[NH:6][C:7]3=[O:22])=[O:20])[CH2:58][CH2:30]2)=[O:36])[CH2:32][CH2:33][CH2:34][CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 166582406-Fluoroquinazoline-2,4(1H,3H)-dioneHCID 683887686-fluoro-1-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dioneHCID 68388893HCID 68388893, compound

Product 1

HCID 683890531-(3-(4-(Cyclohexylcarbonyl)piperazine-1-carbonyl)benzyl)-8-fluoroquinazoline-2,4(1H,3H)-dione

Procedure

The following compounds were prepared from 6-fluoro-1-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dione (prepared from 6-fluoroquinazoline-2,4(1H,3H)-dione and methyl 3-(bromomethyl)benzoate using procedures similar to those of compounds of Examples 1 and 2), and the corresponding substituted piperazine using a procedure similar to those described for the synthesis of compound of Example 3.

Sources & evidence

ORD record
ord-6cc5547763b24302809037b4e85eca5c
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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