Acetyl chloride → HCID 59624715, compound

HRID 1943428Notes

Reaction equation

HRID 1943428 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[H-].[Na+].[C:33](Cl)(=[O:35])[CH3:34]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:33](=[O:35])[CH3:34])[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 59624816HCID 59624816, compound

Product 1

HCID 59624715HCID 59624715, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-chloro-N-(3-fluoropyridin-4-yl)-8-(4-methoxybenzylamino)imidazo[1,2-b]pyridazine-3-carboxamide 19A (80 mg, 0.187 mmol) in DMF (2 mL) was added 60% NaH (18.74 mg, 0.469 mmol). The mixture was stirred for 20 minutes and then a solution of acetyl chloride (0.038 mL, 0.540 mmol) in DMF (0.4 mL) was added, and the mixture was stirred for 30 min. The reaction mixture was quenched with sat. NH4Cl. The light brown solid was collected by filtration, washed with water and dried under vacuum to give 19B (78 mg, 89%). {M+H]=469. HPLC Peak Rt=2.303 minutes (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm.)

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe reaction mixture was quenched with sat. NH4Cl
  3. filtrationThe light brown solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-afc27a77e93c48b39589420b2aeb0ed4
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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