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

HRID 613749Notes

Reaction equation

HRID 613749 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([CH2:17][CH2:18][CH2:19][NH:34][CH2:35][CH2:36][C:37]2[C:45]3[S:44][C:43](=[O:46])[NH:42][C:41]=3[C:40]([OH:47])=[CH:39][CH:38]=2)(=[O:15])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 18779017Methyl 3-[2-[2-(4-fluorophenyl)ethoxy]ethylaminosulphonyl]propanoateHCID 21225700DiisobutylaluminumhydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochloride

Product 1

HCID 18779063N-[2-[2-(4-Fluorophenyl)ethoxy]ethyl]-3-[2-(4-hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethylamino]propanesulphonamide hydrochlorideYield 5.7%

Procedure

The title compound (0.092 g) was prepared according to the method of Example 3e) using methyl 3-[2-[2-(4-fluorophenyl)ethoxy]ethylaminosulphonyl]propanoate (1.0 g), diisobutylaluminiumhydride (1.5M in toluene, 4 ml), 7-(2-aminoethyl)-4-hydroxy-1,3-benzothiazol-2-(3H)-one hydrochloride (0.875 g) and sodium cyanoborohydride (0.354 g).

Sources & evidence

ORD record
ord-1caae8fba5154ce096866221eea54eb1
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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