Sodium cyanoborohydride → AR-C-89855 hydrochloride

HRID 1601736Notes

Reaction equation

HRID 1601736 reaction equation
[CH3:1][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].[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][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:15])=[O:16])=[CH:38][CH:39]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 18779034Methyl 3-[2-[2-(4-methylphenyl)ethoxy]ethylaminosulphonyl]propanoateHCID 21225700DiisobutylaluminumhydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochloride

Product 1

HCID 10218133AR-C-89855 hydrochlorideYield 5%

Procedure

The title compound (0.2 g) was prepared according to the procedure in example 5 part e using methyl 3-[2-[2-(4-methylphenyl)ethoxy]ethylaminosulphonyl]propanoate (2.49 g), diisobutylaluminiumhydride (1.5 M in toluene, 7.5 ml), 7-(2-aminoethyl)4-hydroxy-1,3-benzothiazol-2(3H)-one hydrochloride (2.2 g) and sodium cyanoborohydride (0.48 g).

Sources & evidence

ORD record
ord-6f72351c36d04bbd864df7c5806e123c
Source dataset
uspto-grants-1999_11
Patent number
US05977384

Reaction notes

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