[6-N-(2-methylthioethoxycarbonyl)-adenin-9-yl]-acetic acid → N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[6-N-(2-methylthioethoxycarbonyl)-adenin-9-yl]-acetyl}-glycine ethyl ester

HRID 2222692Notes

Reaction equation

HRID 2222692 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[CH3:2].[CH3:23][S:24][CH2:25][CH2:26][O:27][C:28]([NH:30][C:31]1[N:39]=[CH:38][N:37]=[C:36]2[C:32]=1[N:33]=[CH:34][N:35]2[CH2:40][C:41](O)=[O:42])=[O:29]>>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[C:41](=[O:42])[CH2:40][N:35]1[CH:34]=[N:33][C:32]2[C:36]1=[N:37][CH:38]=[N:39][C:31]=2[NH:30][C:28]([O:27][CH2:26][CH2:25][S:24][CH3:23])=[O:29])[CH3:2]

Participants

3

Reactant 2

HCID 21868391[6-N-(2-methylthioethoxycarbonyl)-adenin-9-yl]-acetic acidHCID 21868443Ethyl 2-((2-(benzo[d]thiazole-2-sulfonamido)ethyl)amino)acetate

Product 1

HCID 21868431N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[6-N-(2-methylthioethoxycarbonyl)-adenin-9-yl]-acetyl}-glycine ethyl esterYield 87%

Procedure

The title compound (2.77 g, 85%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol) and [6-N-(2-methylthioethoxycarbonyl)-adenin-9-yl]-acetic acid (1.56 g, 5 mmol); as per the procedure of Example 20. 1H NMR (500 MHz; DMSO-d6) δ 10.59 (s, 1H), 8.97 (brs, 0.6H), 8.76 (brs, 0.4H), 8.57 (s, 0.4H), 8.52 (s, 0.6H), 8.28 (d, 1H), 8.17 (d, 1H), 7.65 (m, 2H), 5.35 (s, 1.2H), 5.14 (s, 0.8H), 4.46 (s, 0.8H), 4.17 (q, 0.8H), 4.06 (s, 1.2H), 4.02 (q, 1.2H), 3.70 (t, 1.2H), 3.47 (t, 1.2H), 3.42 (t, 0.8H), 3.21 (t, 0.8H), 2.12 (s, 3H), 1.23 (t, 1.2H), 1.12 (t, 1.8H).

Sources & evidence

ORD record
ord-40302a7f210c4aca82dd3cbd303a2ac8
Source dataset
uspto-grants-2008_05
Patent number
US07371859B2

Reaction notes

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