Bromine → HCID 18771692, compound

HRID 479690Notes

Reaction equation

HRID 479690 reaction equation
[Br:1]Br.[CH2:3]([N:5]([CH2:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([NH:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[S:22][CH:23]=2)=[O:17])[CH:12]=[CH:11][CH:10]=1)[CH2:6][CH3:7])[CH3:4]>CO>[Br:1][C:23]1[S:22][C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[N:20][C:19]=1[NH:18][C:16]([NH:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:8][N:5]([CH2:6][CH3:7])[CH2:3][CH3:4])[N:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 10293279HCID 10293279, compound

Product 1

HCID 18771692HCID 18771692, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine (46 μL, 0.90 mmol) was added to a solution of 1-(6-diethylaminomethyl-pyridin-2-yl)-3-(2-pyridin-4-yl-thiazol-4-yl)urea (190 mg, 0.45 mmol, Example 117) in MeOH (8 mL) and the resulting solution was stirred at RT for 1 h. The reaction was quenched with saturated sodium bisulfite solution and concentrated in vacuo. The residue was dissolved in CHCl3/IpOH (3/1, 10 mL) and washed with H2O (3×10 mL) followed by 1N NaOH solution (10 mL). The organics were combined, dried over Na2SO4, and concentrated in vacuo to give a yellow solid. MS m/z: 461.1 (M+H). Calc'd for C19H21BrN6OS-461.39.

Workup

  1. customThe reaction was quenched with saturated sodium bisulfite solution
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3/IpOH (3/1, 10 mL)
  4. washwashed with H2O (3×10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-c8e39913e5444e18b9c49a54218754f1
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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