Allylamine → HCID 86710557, compound

HRID 1027165Notes

Reaction equation

HRID 1027165 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)=[CH:16][CH:17]=1)[C:6](O)=[O:7].[CH2:30]([NH2:33])[CH:31]=[CH2:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[CH2:30]([NH:33][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([C:12]2[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]3[CH2:20][C:21]([CH3:27])([CH3:28])[NH:22][C:23]([CH3:26])([CH3:25])[CH2:24]3)=[CH:16][CH:17]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)[CH:31]=[CH2:32]

Participants

6

Reactant 3

HCID 7853AllylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86710556HCID 86710556, compound

Product 1

HCID 86710557HCID 86710557, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 3-methoxy-4-(6-(methyl(2,2,6,6 tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzoic acid (0.354 mmol) in DMF (4 mL) and CH2Cl2 (4 mL) was added TEA (0.40 mL, 2.83 mmol), allyl amine (0.053 mL, 0.71 mmol), and HATU (202 mg, 0.53 mmol). The crude reaction was allowed to stir at RT overnight. The crude mixture was quenched with sat aq NaHCO3 and diluted with CH2Cl2. The organic layer is washed with water (6×), brine, dried over MgSO4, filtered, and concentrated. The crude product was purified via HPLC to give N-allyl-3-methoxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzamide (8.2 mg). LCMS Rt=1.08 min (condition B); MS (M+1)=438.1

Workup

  1. customThe crude reaction
  2. customThe crude mixture was quenched with sat aq NaHCO3
  3. additiondiluted with CH2Cl2
  4. washThe organic layer is washed with water (6×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified via HPLC

Sources & evidence

ORD record
ord-bd3455cab2904abe832406594422b7a4
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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