Acetic Anhydride → N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162431Notes

Reaction equation

HRID 1162431 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:19](=[O:21])[CH3:20])[N:10]=2)[N:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 497580212-Amino-6-chloroimidazo[1,2-b]pyridazine

Product 1

HCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamideYield 66.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazin-2-amine (18 g, 106.5 mmol) in DCM (180 mL) was added triethylamine (10.8 g, 106.5 mmol), DMAP (1.32 g, 1.06 mmol), and acetic anhydride (6 g, 106.5 mmol) sequentially at rt. The reaction mixture was stirred for 5 h at rt and the precipitate was filtered and washed with 50 mL of methanol to afford the title compound (15 g, 66%). 1H NMR (DMSO-d6, 300 MHz): δ 7.3 (d, 1H), 8.02 (d, 1H), 8.25 (s, 1H). LCMS (M+1) 211 (99%).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with 50 mL of methanol

Sources & evidence

ORD record
ord-174b31240f82450282c5297214fcc8c1
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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