Methanol → 1-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylurea

HRID 9138

Reaction equation

HRID 9138 reaction equation
[C:1]([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])#[N:2].CO>[Pt](=O)=O.C(Cl)(Cl)Cl>[NH2:2][CH2:1][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]

Participants

5

Reactant 2

HCID 887MethanolHCID 219855541-(6-(2-Cyanoacetyl)-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855561-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylureaYield 121.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6212ChloroformSolvent

Procedure

A suspension of 1-(6-(2-cyanoacetyl)-2-benzothiazolyl)-3-ethylurea (0.56 g, 1.94 mmol) and platinum (IV) oxide (0.176 g, 0.78 mmol, 0.40 eq) in 50 mL of 2/3 mixture of MeOH and chloroform was purged and bubbled with hydrogen gas. It was stirred under hydrogen gas for about 2 days. The mixture was filtered and concentrated to give 0.689 g (quantitative yield) desired compound. LC/MS 292.9 (M+1); LC retention time 1.80 min. HPLC purification gave corresponding acetic acid salt. LC/MS 292.9 (M+1); LC retention time 1.80 min. In a similar reaction, compound as an acetate salt form was obtained after HPLC purification.

Workup

  1. customwas purged
  2. custombubbled with hydrogen gas
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec7552d657b74d9cb90ee4e75ae57522
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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