(5-Methyl-2,4-dioxo-1,3-thiazolidin-5-yl)acetic acid → tert-Butyl 2-((5-((2,4-dioxothiazolidin-5-yl)methyl)-1,3,4-oxadiazol-2-yl)methyl)benzo[d]thiazole-6-carboxylate

HRID 1190851Notes

Reaction equation

HRID 1190851 reaction equation
[NH:1]([C:3](=[O:21])[CH2:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[CH:10][C:8]=2[N:9]=1)[NH2:2].C[C:23]1([CH2:30][C:31](O)=O)[S:27][C:26](=[O:28])[NH:25][C:24]1=[O:29]>>[O:28]=[C:26]1[NH:25][C:24](=[O:29])[CH:23]([CH2:30][C:31]2[O:21][C:3]([CH2:4][C:5]3[S:6][C:7]4[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH:11]=[CH:10][C:8]=4[N:9]=3)=[N:1][N:2]=2)[S:27]1

Participants

3

Reactant 2

HCID 3240161(5-Methyl-2,4-dioxo-1,3-thiazolidin-5-yl)acetic acidHCID 86707745tert-Butyl 2-(2-hydrazinyl-2-oxoethyl)benzo[d]thiazole-6-carboxylate

Product 1

HCID 86707746tert-Butyl 2-((5-((2,4-dioxothiazolidin-5-yl)methyl)-1,3,4-oxadiazol-2-yl)methyl)benzo[d]thiazole-6-carboxylateYield 38%

Procedure

Compound 188d was prepared from Compound 188c in 38% yield as a white solid using the general procedure given for Compound 1a. LCMS=1.88 min using analytical method (B), 447.0 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J=1.1 Hz, 1H), 8.14 (dd, J=8.6, 1.5 Hz, 1H), 8.04 (d, J=8.6 Hz, 1H), 4.82 (dd, J=9.2, 4.2 Hz, 1H), 4.76 (s, 2H), 3.82-3.76 (m, 1H), 3.49 (m, 1H), 1.64 (s, 9H).

Workup

  1. customLCMS=1.88 min

Sources & evidence

ORD record
ord-1478551f5ef04fa79c01af1d58647a53
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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