Methylamine → 3-(1-(isopropylamino)phthalazin-6-yl)-N,4-dimethylbenzamide

HRID 2357537Notes

Reaction equation

HRID 2357537 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:18]([OH:20])=O)=[CH:12][CH:13]=2)[CH:8]=[N:7][N:6]=1)([CH3:3])[CH3:2].CN.[CH3:27][N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:18]([NH:28][CH3:27])=[O:20])=[CH:12][CH:13]=2)[CH:8]=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684556533-(1-(Isopropylamino)phthalazin-6-yl)-4-methylbenzoic acid

Product 1

HCID 684548743-(1-(isopropylamino)phthalazin-6-yl)-N,4-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoic acid (0.22 g, 0.7 mmol) in DMF (2 mL) at RT was treated with a 2 M solution of methylamine (2 mL, 3 mmol), and HATU (0.4 g, 1 mmol). The mixture was stirred at RT for 15 h. The mixture was diluted with 100 mL DCM, washed with 20 mL sat. NaHCO3, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column eluting with 2-3% 2M ammonia MeOH/DCM to give the title compound. MS (ES+): 335 (M+H)+.

Workup

  1. washwashed with 20 mL sat. NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column
  5. washeluting with 2-3% 2M ammonia MeOH/DCM

Sources & evidence

ORD record
ord-01a9ce46d5954e8f8a8dbce623c73db6
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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