Hydrogen Bromide → HCID 131728331, compound

HRID 1715236Notes

Reaction equation

HRID 1715236 reaction equation
[C:1]([C:4]1[S:8][C:7]([N:9]([C:13]2[CH:17]=[CH:16][N:15]([C:18](=[O:20])[CH3:19])[N:14]=2)C(=O)C)=[N:6][C:5]=1[CH3:21])(=[O:3])[CH3:2].[BrH:22].BrBr>CC(O)=O>[BrH:22].[C:18]([N:15]1[CH:16]=[CH:17][C:13]([NH:9][C:7]2[S:8][C:4]([C:1](=[O:3])[CH2:2][Br:22])=[C:5]([CH3:21])[N:6]=2)=[N:14]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 68411569HCID 68411569, compound

Product 1

HCID 131728331HCID 131728331, compoundYield 1,491.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
60 °C

Procedure

N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N-(1-acetyl-1H-pyrazol-3-yl)acetamide (689.3 mg; 2.25 mmol; 1 eq.) is dissolved in AcOH (10 ml) and hydrobromic acid (39 μl; 0.22 mmol; 0.10 eq.). A solution of bromine (115 μl; 2.25 mmol; 1 eq.) in AcOH (2 ml) is added dropwise. The reaction mixture is stirred 3 h at rt and 2 h at 60° C. In order to complete the reaction, a solution of bromine (58 μl; 1.12 mmol; 0.50 eq.) in AcOH (2 ml) is added and the mixture is stirred 4 h at 60° C. It is cooled down to rt and the resulting precipitate is filtered, washed with cyclohexane and dried under reduced pressure to give, affording Intermediate 4 (695.7 mg; 73%). It is used in bis-thiazol 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 2.57 (s, 3H), 2.64 (s, 3H), 4.63 (s, 2H), 6.36 (d, J=6 Hz, 1H), 8.35 (d, J=6 Hz, 1H). M− (ESI): 342.96; M+ (ESI): 344.94. HPLC (Method A), Rt: 3.08 min (purity: 91.91%).

Workup

  1. customthe reaction
  2. stirringthe mixture is stirred 4 h at 60° C
  3. temperatureIt is cooled down to rt
  4. filtrationthe resulting precipitate is filtered
  5. washwashed with cyclohexane
  6. customdried under reduced pressure
  7. customto give

Sources & evidence

ORD record
ord-601b3bf3a02d4183bad081acdf0c659e
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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