Chloroacetone → HCID 11615485, compound

HRID 1371570Notes

Reaction equation

HRID 1371570 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[NH:8])=[N:4][O:5][N:6]=1.Cl[CH2:15][C:16](=O)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:10]([N:9]1[CH:15]=[C:16]([CH3:17])[N:8]=[C:7]1[C:3]1[C:2]([NH2:1])=[N:6][O:5][N:4]=1)[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 178449179HCID 178449179, compound

Product 1

HCID 11615485HCID 11615485, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine (38 mg, 0.2 mmol), 1-chloropropanone (37 mg, 0.4 mmol) and potassium carbonate (55 mg, 0.4 mmol) in DMF (0.5 mL) was microwaved for 20 minutes at 180° C. The crude mixture was purified via Gilson and then a flash pipette column to afford the title compound as a white solid 2.5 mg. HPLC Rt 5.6 min; MS 222.1 as M+1 peak; HPLC Method B Rt 3.4 min. 1HNMR (CDCl3) 6.94 (s, 1H); 5.73 (br, 2H); 4.15 (d, 2H); 2.3 (s, 3H); 2.15 (m, 1H); 0.95 (d, 6H).

Workup

  1. customwas microwaved for 20 minutes at 180° C
  2. customThe crude mixture was purified via Gilson

Sources & evidence

ORD record
ord-ccb249c82ebc478699d080a13c0e7edf
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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