Water → HCID 25207803, compound

HRID 2272936Notes

Reaction equation

HRID 2272936 reaction equation
Cl[C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1.[CH3:26][NH2:27].O>CC(N(C)C)=O>[CH3:26][NH:27][C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 46883208HCID 46883208, compound

Product 1

HCID 25207803HCID 25207803, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A stirred solution of Example 5 (0.4 g, 1 mmol) in dimethyl acetamide (10 ml) was treated with methylamine (2.0M in MeOH, 4.96 ml, 1.10 mmol). The solution was heated to 150° C. in a sealed tube for 1 h. The solution was cooled to room temperature and slowly poured onto stirred iced water (100 ml). After 15 min stirring, a light orange solid was filtered. Recrystallisation from hot ethyl acetate gave the title compound in 58% yield, >95% purity. LC-MS m/z=382.0 [M+H]+; RT=2.73; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 2.89 (3H, d, J 5.0 Hz), 4.67 (2H, d, J 6.0 Hz), 5.81 (1H, s), 7.23 (1H, t, J 4.5 Hz), 7.77 (1H, d, J 8.0 Hz), 7.96 (1H, b), 8.09 (1H, d, J=5.0 Hz), 8.41 (1H, d, J=5.0 Hz), 8.36-8.50 (1H, b), 8.61 (1H, bd)

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additionslowly poured
  3. filtrationa light orange solid was filtered
  4. customRecrystallisation from hot ethyl acetate

Sources & evidence

ORD record
ord-a4a9c6193cba447ca305f9d3a4d9f6ce
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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