4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 86614384, compound

HRID 641345Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:17]3[CH:18]=[C:19]([C:22](O)=[O:23])[CH:20]=[CH:21][C:16]=3[O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH2:25][C:26]1[S:27][CH:28]=[C:29]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:30]=1>>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][C:29]1[N:30]=[C:26]([NH:25][C:22]([C:19]2[CH:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]([S:9]([C:4]4[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=4)(=[O:10])=[O:11])[C:17]=3[CH:18]=2)=[O:23])[S:27][CH:28]=1)[CH3:36]

Participants

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

HCID 66790214HCID 66790214, compound

Product 1

HCID 86614384HCID 86614384, compound

Procedure

The title compound, MS (ISP)=486.3 (M−H)−, was produced as described in example 1, steps 1-6. Step 3 was performed using 3,5-dimethylbenzenesulfonyl chloride, furnishing 4-(3,5-Dimethyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester, which was hydrolyzed in step 4, leading to 4-(3,5-dimethyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid. This was reacted with ethyl 2-amino-4-thiazoleacetate in step 5 and yielded (2-{[4-(3,5-dimethyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-a57c9e26a9a74d108d832ce7fbdac453
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696200B2

Reaction notes

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