Sodium triacetoxyborohydride → N-(indan-2-yl)-5-(propyl-(4,5,6,7-tetrahydrobenzothiazol-6-yl)amino)pentanamide

HRID 1942413Notes

Reaction equation

HRID 1942413 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1)[CH2:2][CH3:3].[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[NH:23][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH:28]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[NH:23][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amineHCID 86651316N-(indan-2-yl)-5-oxopentanamide

Product 1

HCID 42602944N-(indan-2-yl)-5-(propyl-(4,5,6,7-tetrahydrobenzothiazol-6-yl)amino)pentanamideYield 66%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 395 mg (2 mmol) propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine and 694 mg (3 mmol) N-(2,3-dihydro-1H-inden-2-yl)-5-oxopentanamide in 1,2-dichloroethane (20 mL) is stirred for about 30 minutes. Then 0.75 g (3 mmol) of sodium triacetoxyborohydride is added and the mixture is stirred overnight. After hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated, dried over sodium sulfate and concentrated in vacuum. The crude product obtained is purified via column chromatography on silica gel.

Workup

  1. customAfter hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-8aaddfce57ba4daa89799b96b1c58a7d
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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