Methyl p-toluenesulfonate → HCID 73855118, compound

HRID 1242015Notes

Reaction equation

HRID 1242015 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12](SC)=[N:11][C:10]=2[CH:16]=1.[C:17]1(C)C=CC(S(OC)(=O)=O)=CC=1.[CH2:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:43])[CH2:40][O:41][CH3:42])=[CH:34][C:33]=1[N:44]=[C:45]1[N:49]([CH2:50][C:51]2[O:52][CH:53]=[CH:54][CH:55]=2)[C:48](=[O:56])[CH2:47][S:46]1)[CH3:30]>>[CH2:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:43])[CH2:40][O:41][CH3:42])=[CH:34][C:33]=1[N:44]=[C:45]1[N:49]([CH2:50][C:51]2[O:52][CH:53]=[CH:54][CH:55]=2)[C:48](=[O:56])[C:47](=[C:12]2[N:11]([CH3:17])[C:10]3[CH:16]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[CH:8][C:9]=3[S:13]2)[S:46]1)[CH3:30]

Participants

4

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 21937404HCID 21937404, compoundHCID 21937486HCID 21937486, compound

Product 1

HCID 73855118HCID 73855118, compound

Procedure

In a manner similar to Example 156, 5-(2-methoxyethoxy)-2-(methylthio)benzothiazole was alkylated with methyl p-toluenesulfonate and then condensed with intermediate N-[4-ethylamino-3-(3-furan-2-ylmethyl-4-oxothiazolidin-2-ylideneamino)phenyl]-2-methoxyacetamide. 1H-NMR (CDCl3): δ 8.09 (1H, s), 7.28–7.38 (3H, m), 7.15 (1H, dd), 6.76 (1H, dd), 6.64 (1H, d), 6.44 (1H, d), 6.33 (1H, m), 5.16 (2H, s), 4.14 (2H, m), 4.01 (2H, s), 3.77 (2H, m), 3.72 (3H, s), 3.51 (3H, s), 3.44 (3H, s), 3.15 (2H, q), 1.23 (3H, t); MS(ESI): 624(MH+).

Sources & evidence

ORD record
ord-159c5e1a641d441988f38b2aa22e51d8
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

Loading…