Chloroacetyl chloride → HCID 58886676, compound

HRID 494735Notes

Reaction equation

HRID 494735 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([NH:17][NH2:18])=[O:16])=[CH:13][N:12]3[CH:19]=[CH:20][N:21]=[C:11]3[C:10]=2[Cl:22])=[C:4]([F:23])[CH:3]=1.[Cl:24][CH2:25][C:26](Cl)=[O:27]>ClCCl.C(OCC)(=O)C>[Cl:24][CH2:25][C:26]([NH:18][NH:17][C:15]([C:14]1[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:23])=[C:10]([Cl:22])[C:11]2[N:12]([CH:19]=[CH:20][N:21]=2)[CH:13]=1)=[O:16])=[O:27]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 58886642HCID 58886642, compound

Product 1

HCID 58886676HCID 58886676, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

7-(4-Bromo-2-fluorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid hydrazide (100 mg, 0.25 mmol) of Step A, Example 35 was suspended in dichloromethane (2 mL) and 4-Me morpholine (0.040 mL, 0.36 mmol) was added. The mixture was cooled to 0° C. and then chloroacetyl chloride (0.029 mL, 0.36 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour under N2. Rinsed reaction mixture into a separatory funnel with a small amount of tetrahydrofuran and methanol and then diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous NaCl, dried over Na2SO4 and concentrated. Purification of the crude product was achieved by flash column chromatography (20:1 dichloromethane/methanol) to yield the desired product (64 mg, 54%) as a yellow solid. MS ESI (+) m/z 474, 476 (M+, Cl, Br pattern) detected.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washRinsed
  3. customreaction mixture into a separatory funnel with a small amount of tetrahydrofuran and methanol
  4. washThe organic layer was washed with water and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification of the crude product

Sources & evidence

ORD record
ord-06f2700854d3460abfe24d29812bbca9
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

Loading…