Trifluoroacetic acid → N-[5-(6-aminoimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide

HRID 539802Notes

Reaction equation

HRID 539802 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([NH:16]CC4C=C(OC)C(OC)=C(OC)C=4)=[N:12][N:11]3[CH:30]=2)=[CH:4][C:3]=1[NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34].C(O)(C(F)(F)F)=O>>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2=[N:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:31][C:32](=[O:37])[C:33]([CH3:34])([CH3:35])[CH3:36])[CH:4]=3)=[CH:30][N:11]2[N:12]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67983329N-(2-methyl-5-(6-(3,4,5-trimethoxybenzylamino)imidazo[1,2-b]pyridazin-2-yl)phenyl)pivalamide

Product 1

HCID 67983095N-[5-(6-aminoimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamideYield 90.2%

Conditions

Temperature
50 °C

Procedure

A 40-mL vial is charged with N-(2-methyl-5-(6-(3,4,5-trimethoxybenzylamino)imidazo[1,2-b]pyridazin-2-yl)phenyl)pivalamide (0.604 g, 1.2 mmol) and TFA (5 mL) and the mixture is stirred at 50° C. for 16 hours. The reaction mixture is concentrated, taken up in CH3CN and water is added. The mixture is concentrated to form solid from aqueous solution. The mixture is frozen and water is removed on a lyophilizer to afford the title compound (0.350 g). LCMS (m/z)=324.5 [M+H]+, tR=1.96 min.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionwater is added
  3. concentrationThe mixture is concentrated
  4. customto form solid from aqueous solution
  5. temperatureThe mixture is frozen
  6. customwater is removed on a lyophilizer

Sources & evidence

ORD record
ord-1b9a8b9cbf8b41479662168055907838
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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