Hydrogen Bromide → HCID 131728330, compound

HRID 1715232Notes

Reaction equation

HRID 1715232 reaction equation
[C:1]([C:4]1[S:8][C:7]([N:9]([C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)C(=O)C)=[N:6][C:5]=1[CH3:19])(=[O:3])[CH3:2].[BrH:20].BrBr>CC(O)=O>[BrH:20].[Br:20][CH2:2][C:1]([C:4]1[S:8][C:7]([NH:9][C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)=[N:6][C:5]=1[CH3:19])=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 68409396HCID 68409396, compound

Product 1

HCID 131728330HCID 131728330, compoundYield 1,249.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
60 °C

Procedure

N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N-pyrazin-2-ylacetamide (511.2 mg; 1.85 mmol; 1 eq.) is dissolved in AcOH (10 ml). Hydrobromic acid (32 μl; 0.19 mmol; 0.10 eq.) is added, followed by a solution of bromine (95 μl; 1.85 mmol; 1 eq.) in AcOH (2 ml). The mixture is stirred 3 h at rt and 2 h at 60° C. To complete the reaction, bromine (95 μl; 1.85 mmol; 1 eq.) in AcOH (2 ml) is added and the mixture is stirred 4 h at 60° C. Solvents are evaporated and the resulting dark brown solid is suspended in THF, filtered and washed with cyclohexane, affording Intermediate 3 as yellow solid (467.7 mg; 64%). It is used in bisthiazol synthesis as HBr salt or as parent, after 5 min treatment with Amberlyst A21 in DCM/MeOH mixture. 1H NMR (DMSO-d6, 300 MHz) δ 2.60 (s, 3H), 4.64 (s, 2H), 8.24 (d, J=2.6 Hz, 1H), 8.43 (dd, J=1.5 Hz, J=2.6 Hz, 1H), 8.50 (d, J=1.5 Hz, 1H). M+ (ESI): 312.9. HPLC (Method A), Rt: 2.80 min (purity: 97%).

Workup

  1. additionis added
  2. stirringthe mixture is stirred 4 h at 60° C
  3. customSolvents are evaporated
  4. filtrationfiltered
  5. washwashed with cyclohexane

Sources & evidence

ORD record
ord-0308dbf4b7b34fcfb6aaa68fe945fef5
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

Loading…