Trifluoroacetic acid → HCID 86657955, compound

HRID 1036247Notes

Reaction equation

HRID 1036247 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12]C(C)(C)C)=O)[CH:5]=[N:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O.[NH2:24][C:25]1[N:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][N:34]([C:37](=[O:39])[CH3:38])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(Cl)Cl>[C:37]([N:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:10](=[O:12])[CH2:9][C:4]3[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[N:30][CH:29]=2)[CH2:36][CH2:35]1)(=[O:39])[CH3:38]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 284116891-(4-(6-Aminopyridin-3-YL)piperazin-1-YL)ethan-1-oneHCID 58447890HCID 58447890, compound

Product 1

HCID 86657955HCID 86657955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(5,6-dichloropyridin-3-yl)acetate 184-3 (130 mg, 0.49 mmol) and TFA (0.5 mL) in DCM (3 mL) was stirred at room temperature for 2 hours. The solvents were evaporated to dryness under high vacuum. The crude product, 2-(5,6-dichloropyridin-3-yl)acetic acid 184-4, was dissolved in DMF (3 mL). 1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethanone (128 mg, 0.58 mmol) and DIEA (435 uL, 2.5 mmol) were added to the solution before O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (277 mg, 0.73 mmol). The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation. The residue was purified by silica gel flash chromatography and eluted with 5% MeOH in CH2Cl2 to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(5,6-dichloropyridin-3-yl)acetamide 184-5. MS m/z 408.1 (M+1).

Workup

  1. customThe solvents were evaporated to dryness under high vacuum
  2. dissolutionThe crude product, 2-(5,6-dichloropyridin-3-yl)acetic acid 184-4, was dissolved in DMF (3 mL)
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe solvent was removed by rotary evaporation
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f124c04584f145aeb5a0002b2369c03c
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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