Dimethylformamide → N-Cyclopropyl-3-(1-isopropylphthalazin-6-yl)-4-methylbenzamide

HRID 2357544Notes

Reaction equation

HRID 2357544 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:17]([OH:19])=O)=[CH:11][CH:12]=2)[CH:7]=[N:6][N:5]=1)([CH3:3])[CH3:2].CN(C(ON1N=NC2[CH:35]=[CH:36][CH:37]=[N:38]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C=O.C1(N)CC1>C(OCC)(=O)C>[CH:37]1([NH:38][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:14]([C:10]3[CH:9]=[C:8]4[C:13](=[CH:12][CH:11]=3)[C:4]([CH:1]([CH3:2])[CH3:3])=[N:5][N:6]=[CH:7]4)[CH:15]=2)[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684522933-(1-Isopropylphthalazin-6-yl)-4-methylbenzoic acid

Product 1

HCID 68452802N-Cyclopropyl-3-(1-isopropylphthalazin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 10-mL round-bottom flask was charged with 3-(1-isopropylphthalazin-6-yl)-4-methylbenzoic acid (32 mg, 0.10 mmol), HATU (60 mg, 0.157 mmol), and N,N-dimethylformamide (0.5 mL), followed by cyclopropylamine (0.03 mL, 0.52 mmol). The resulting golden yellow mixture was stirred at RT for 18 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine, then dried (MgSO4) and concentrated in vacuo. CombiFlash purification (20% to 70% ethyl acetate in Hexane) afforded the title compound as an off-white amorphous solid. MS (ES+): 346.2 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customCombiFlash purification (20% to 70% ethyl acetate in Hexane)

Sources & evidence

ORD record
ord-73a52676640b4e7ba6c84383ea6ae339
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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