Dichloromethane → HCID 86624706, compound

HRID 604922Notes

Reaction equation

HRID 604922 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:18]([CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)O)=[CH:19][N:20]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C(Cl)Cl>>[CH2:21]([C:18]1[S:17][C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:20][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 25107426HCID 25107426, compound

Product 1

HCID 86624706HCID 86624706, compoundYield 98%

Procedure

To a solution of 35 mg (0.09 mmol) {2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-5-yl}-phenyl-methanol in methylene chloride (2 ml) 12 mg (0.1 mmol) triethylsilane was added at room temperature and trifluoro acetate (2 ml) was added. The reaction was stirred at room temperature for 6 hours and the solvent was evaporated under reduced pressure. The residue was suspended in saturated aqueous sodium hydrogen carbonate solution and extracted twice with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulphate, filtered and the solvent was evaporated under reduced pressure to yield 33 mg (98%) (5-benzyl-thiazol-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a brown solid. MS ISP (m/e): 377.4 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.64 (s, 1H), 7.53 (s, 1H), 7.35-7.22 (m, 7H), 7.07 (s, 1H), 7.01 (s, 1H), 4.03 (s, 2H), 3.77 (s, 3H), 2.13 (s, 3H).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionextracted twice with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-99d13d3d5a614467adf0d339ce33e256
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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