Benzene, ((2-bromoethoxy)methyl)- → N-(2-(2-(benzyloxy)ethylamino)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl)-3,5-dimethoxy-4-methylbenzamide

HRID 1296760Notes

Reaction equation

HRID 1296760 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.Br[CH2:30][CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CC1ON=C(C2C=CC(CNC(=O)C3C=C(OC)C(C)=C(OC)C=3)=C(NCCOC3C=CC=CC=3)C=2)N=1>>[CH2:33]([O:32][CH2:31][CH2:30][NH:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 69489603N-(4-(5-methyl-1,2,4-oxadiazol-3-yl)-2-(2-phenoxyethylamino)benzyl)-3,5-dimethoxy-4-methylbenzamideHCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 69491573N-(2-(2-(benzyloxy)ethylamino)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl)-3,5-dimethoxy-4-methylbenzamideYield 51%

Procedure

Compound 1g was reacted with benzyl 2-bromoethyl ether according to the procedure described in compound 42a, to give compound 51a (79 mg, 51%). ESI-MS m/e 517.4 (M+1).

Sources & evidence

ORD record
ord-5617daa85b894a6e850df31ecfb3b3f0
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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