HCID 59854220, compound → HCID 59854175, compound

HRID 2374699Notes

Reaction equation

HRID 2374699 reaction equation
[NH2:1][C:2]1[C:3]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:26]([C:29]1[S:33][CH:32]=[N:31][C:30]=1Br)(=O)[CH3:27]>>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[C:26]([CH3:27])=[C:29]3[S:33][CH:32]=[N:31][C:30]3=[N:1][C:2]=2[C:3]=1[O:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:6]

Participants

3

Reactant 2

HCID 59854220HCID 59854220, compoundHCID 59854253HCID 59854253, compound

Product 1

HCID 59854175HCID 59854175, compound

Procedure

For example, methyl 3-amino-2-diphenylmethoxybenzoate A27.12 is reacted with 5-acetyl-4-bromothiazole A27.13 (WO 9317681) to afford after cyclization of the initial displacement product, 5-benzhydryloxy-9-methyl-thiazolo[4,5-b]quinoline-6-carboxylic acid methyl ester A27.14. Reaction with N-bromosuccinimide in hexachloroethane then yields the bromomethyl analog A27.15, and this material is reacted with a trialkyl phosphite in an Arbuzov reaction to give the phosphonate A27.16. The product is then reacted with 3,5-dichlorobenzyl methylamine A27.17 and trimethyl aluminum to afford after deprotection the phosphonate A27.18.

Sources & evidence

ORD record
ord-2ffb4644124f47e2ad802d0c0d5f9ef5
Source dataset
uspto-grants-2008_12
Patent number
US07462721B2

Reaction notes

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