Sodium cyanoborohydride → 3-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)-ethylamino]-N-[2-(2-phenylthioethoxy)ethyl]propanesulphonamide hydrochloride

HRID 613760Notes

Reaction equation

HRID 613760 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([CH2:17][CH2:18][C:19](OC)=O)(=[O:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[ClH:33].[NH2:34][CH2:35][CH2:36][C:37]1[C:45]2[S:44][C:43](=[O:46])[NH:42][C:41]=2[C:40]([OH:47])=[CH:39][CH:38]=1.C([BH3-])#N.[Na+]>>[ClH:33].[OH:47][C:40]1[C:41]2[NH:42][C:43](=[O:46])[S:44][C:45]=2[C:37]([CH2:36][CH2:35][NH:34][CH2:19][CH2:18][CH2:17][S:14]([NH:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:15])=[O:16])=[CH:38][CH:39]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 18779027Methyl 3-[2-(2-phenylthioethoxy)ethylaminosulphonyl]propanoateHCID 21225700DiisobutylaluminumhydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochloride

Product 1

HCID 187790703-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)-ethylamino]-N-[2-(2-phenylthioethoxy)ethyl]propanesulphonamide hydrochlorideYield 4.8%

Procedure

The title compound (0.106 g) was prepared according to the procedure in example 8 part e using methyl 3-[2-(2-phenylthioethoxy)ethylaminosulphonyl]propanoate (1.4 g), diisobutylaluminiumhydride (1.5M in toluene, 3 ml), 7-(2-aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrochloride (1.2 g) and sodium cyanoborohydride (0.3 g).

Sources & evidence

ORD record
ord-944d86a55a9e43678252c884fd3ff570
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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