Benzoyl chloride → N1-[3-(2-{[(Ethylamino)carbonyl]amino}-1,3-benzothiazol-6-yl)-3-oxopropyl]benzamide

HRID 9139

Reaction equation

HRID 9139 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5].C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:17]([NH:16][C:14]([NH:13][C:11]1[S:12][C:8]2[CH:7]=[C:6]([C:4](=[O:5])[CH2:3][CH2:2][NH:1][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:20]=[CH:19][C:9]=2[N:10]=1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 219855561-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 21985596N1-[3-(2-{[(Ethylamino)carbonyl]amino}-1,3-benzothiazol-6-yl)-3-oxopropyl]benzamideYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea (0.033 g, 0.10 mmol) in 1 mL anhydrous DMF was treated with triethylamine (0.028 mL, 0.20 mmol, 2.0 eq) at room temperature. It was stirred for about 5 min, followed by the addition of benzoyl chloride (0.014 mL, 0.12 mmol, 1.2 eq). It was stirred for about 2.5 hours, quenched with MeOH, filtered, concentrated, and purified by HPLC to give the desired compound 0.011 g (28%). LC/MS 396.7 (M+1); LC retention time 2.74 min.

Workup

  1. stirringIt was stirred for about 2.5 hours
  2. customquenched with MeOH
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-d4a430f6fb924fac95a71637b5597afc
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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