Triethylamine → HCID 71232709, compound

HRID 869471Notes

Reaction equation

HRID 869471 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C@H:12]([C:14]2[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16](=[O:28])[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])[CH3:13])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C(N(CC)CC)C>CO.[Pd]>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[C:4]([NH:11][C@H:12]([C:14]1[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16](=[O:28])[C:17]3[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:26])([F:27])[F:25])[CH3:13])=[CH:3][CH:2]=[N:7]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86676287HCID 86676287, compound

Product 1

HCID 71232709HCID 71232709, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of (S)-3-(1-(6-chloroimidazo[1,2-b]pyridazin-8-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-7 (50 mg, 0.104 mmol, 1.0 eq) in MeOH (20 mL), palladium on carbon (10%, 17 mg) and triethylamine (0.1 mL, 0.72 mmol, 6.9 eq) were added. The resulting mixture was degassed and back-filled with hydrogen (three cycles), and then stirred at RT under hydrogen overnight. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5-10% ethyl acetate-petroether) to afford the product, (S)-3-(1-(imidazo[1,2-b]pyridazin-8-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-8. ESI-MS m/z: 450.2 [M+H]+.

Workup

  1. customThe resulting mixture was degassed
  2. additionback-filled with hydrogen (three cycles)
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (5-10% ethyl acetate-petroether)

Sources & evidence

ORD record
ord-1f197d1d25b842a4a6df8609646c2b75
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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