Dichloromethane → 1-(4-(3-(Aminomethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-fluorophenyl)pyrrolidin-2-one

HRID 219110Notes

Reaction equation

HRID 219110 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[N:21][N:22]=3)[N:19]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:24][CH2:23][C:20]1[N:18]2[N:19]=[C:14]([C:4]3[CH:5]=[CH:6][C:7]([N:8]4[CH2:12][CH2:11][CH2:10][C:9]4=[O:13])=[C:2]([F:1])[CH:3]=3)[CH:15]=[CH:16][C:17]2=[N:22][N:21]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57691433Tert-butyl (6-(3-fluoro-4-(2-oxopyrrolidin-1-yl)phenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 576912831-(4-(3-(Aminomethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-fluorophenyl)pyrrolidin-2-one

Procedure

A 50 mL recovery flask was charged with tert-butyl (6-(3-fluoro-4-(2-oxopyrrolidin-1-yl)phenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.117 g, 0.274 mmol), TFA (0.0211 ml, 0.274 mmol), and DCM (0.0177 ml, 0.274 mmol), then stirred open to air at room temperature for 2 hours. The mixture was concentrated, then taken up in MeOH. K2CO3 was added, and this was stirred for 1 hour. The mixture was concentrated, then the residue was taken up in MeOH/CHCl3 then filtered. The filtrate was evaporated, taken up in water, then passed through a reverse phase C18 column, eluting with MeOH/DCM, then concentrated.

Workup

  1. concentrationThe mixture was concentrated
  2. additionK2CO3 was added
  3. stirringthis was stirred for 1 hour
  4. concentrationThe mixture was concentrated
  5. filtrationthen filtered
  6. customThe filtrate was evaporated
  7. washeluting with MeOH/DCM
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d135b2356beb4833abb0e39f5a2c486d
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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