Acetic Acid → HCID 16035071, compound

HRID 2234186Notes

Reaction equation

HRID 2234186 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([N:15]([CH2:24][CH:25]=O)[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])=[CH:4][CH:3]=1.Cl.[NH2:28][CH2:29][CH2:30][C:31]1[C:39]2[S:38][C:37](=[O:40])[NH:36][C:35]=2[C:34]([OH:41])=[CH:33][CH:32]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([N:15]([CH2:24][CH2:25][NH:28][CH2:29][CH2:30][C:31]2[C:39]3[S:38][C:37](=[O:40])[NH:36][C:35]=3[C:34]([OH:41])=[CH:33][CH:32]=2)[CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:14])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochlorideHCID 86625181HCID 86625181, compound

Product 1

HCID 16035071HCID 16035071, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-[2-(4-Bromophenyl)ethoxy]-N-(2-oxoethyl)-N-phenethyl-propanamide (Example 10d), 0.54 g) was dissolved in methanol (25 mL) and treated with 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.32 g), acetic acid (0.5 mL) and water (1.5 mL). The resultant mixture was stirred at room temperature for 2 hours and then sodium cyanoborohydride (0.05 g) was added and the reaction mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in methanol (25 mL) and adsorbed onto silica gel. The adsorbed mixture was purified by flash chromatography to yield the titled compound (0.51 g) as a crystalline yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe adsorbed mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-0d0ed39adcb849acaa001386fc8d5306
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

Loading…