Benzyl Bromide → HCID 23287696, compound

HRID 367135Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]=2[S:5][C:4]([NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)=[N:3]1.[H-].[Li+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:3]1[C:2](=[O:1])[C:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]=2[S:5][C:4]1=[N:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 62714Lithium hydride

HCID 1259240HCID 1259240, compound

Product 1

HCID 23287696HCID 23287696, compound

Procedure

The reaction procedure of Example 11 was followed except that 1.31 g of ethyl 4-[(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino]benzoate, 36 mg of lithium hydride and 0.48 ml of benzyl bromide were used. As a result, 1.28 g of ethyl 4-[(3-benzyl-4-oxo-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-2-ylidene)amino]benzoate was obtained as a low polarity substance, and 20 mg of ethyl 4-[N-benzyl-N-(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino]benzoate was obtained as a high polarity substance.

Workup

customThe reaction procedure of Example 11

Sources & evidence

ORD record: ord-6fbe60f0bfeb4023b7f67024bc0ebe5b
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133258

Reaction notes

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