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

HRID 613756Notes

Reaction equation

HRID 613756 reaction equation
[C:1]1([CH:7]([CH3:22])[CH2:8][O:9][CH2:10][CH2:11][NH:12][S:13]([CH2:16][CH2:17][C:18](OC)=O)(=[O:15])=[O:14])[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][CH2:18][CH2:17][CH2:16][S:13]([NH:12][CH2:11][CH2:10][O:9][CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:22])(=[O:14])=[O:15])=[CH:38][CH:39]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 18779042Methyl 3-[2-(2-phenyl-1-propoxy)ethylaminosulphonyl]propanoateHCID 21225700DiisobutylaluminumhydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochloride

Product 1

HCID 187790503-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethylamino]-N-[2-(2-phenyl-1-propoxy)ethyl]propanesulphonamide hydrochlorideYield 10.1%

Procedure

The title compound (0.164 g) was prepared according to the procedure in example 5 part e using methyl 3-[2-(2-phenyl-1-propoxy)ethylaminosulphonyl]propanoate (1.01 g), diisobutylaluminiumhydride (1.5M in toluene, 3 ml), 7-(2-aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrochloride (0.89 g) and sodium cyanoborohydride (0.19 g).

Sources & evidence

ORD record
ord-9473385cd8f34196b6e62e956fd236ec
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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