Trifluoroacetic acid → HCID 57691248, compound

HRID 1511377Notes

Reaction equation

HRID 1511377 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][NH:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][N:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:31][NH:32]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(#N)C.O.[OH-].[Na+]>[NH2:32][CH2:31][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][NH:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][N:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67967034Tert-butyl (2-chloro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methylcarbamate

Product 1

HCID 57691248HCID 57691248, compound

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 6344DichloromethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
23 °C

Procedure

To a stirring solution of tert-butyl (2-chloro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methylcarbamate (70 mg, 128 μmol) in DCM (2 mL) was added TFA (2 mL). Reaction solution stirred for 30 min at 23° C. Solvents then removed under reduced pressure and residue purified on prep-HPLC using a water/ACN (0.1% TFA) gradient. Resulting solid was dissolved in 1:1 ACN/water (1 mL) and pH adjusted to 10 with 1M NaOH (approx 10 drops). Resulting solid collected by filtraton and washed with water (5 mL). MS (ESI pos. ion) m/z: 447 (MH+). Calc'd exact mass for C22H19ClN8O: 446.

Workup

  1. customReaction solution
  2. customSolvents then removed under reduced pressure and residue
  3. custompurified
  4. customResulting solid
  5. customResulting solid
  6. customcollected by filtraton
  7. washwashed with water (5 mL)

Sources & evidence

ORD record
ord-c9fcda9e13284361981c4a252264c6be
Source dataset
uspto-grants-2012_07
Patent number
US08212041B2

Reaction notes

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