HCID 58886676, compound → HCID 21111547, compound

HRID 1766821Notes

Reaction equation

HRID 1766821 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7]([C:9]1[C:10]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])=[C:11]([Cl:18])[C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1)=O)=[O:4]>O=P(Cl)(Cl)Cl>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:10]2[C:9]([C:7]3[O:4][C:3]([CH2:2][Cl:1])=[N:5][N:6]=3)=[CH:14][N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11]=2[Cl:18])=[C:21]([F:27])[CH:22]=1

Participants

3

Reactant 1

HCID 58886676HCID 58886676, compound

Product 1

HCID 21111547HCID 21111547, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

7-(4-Bromo-2-fluorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid N′-(2-chloro-acetyl)-hydrazide (63 mg, 0.13 mmol) was suspended in POCl3 (1 mL). The reaction mixture was heated to 100° C. for 8 hours, during which time it became a bright red solution. The reaction mixture was cooled to room temperature and the solvent evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried over Na2SO4 and concentrated. The crude product (38 mg, 62%) was used without further purification in next step. MS ESI (+) m/z 456, 458 (M+, Cl, Br pattern) detected.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3, saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product (38 mg, 62%) was used without further purification in next step

Sources & evidence

ORD record
ord-c2561fddbc1342d9943fc6e1957fce89
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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