Cyclopropylamine → (+/-) N-Cyclopropyl-4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzamide

HRID 422560Notes

Reaction equation

HRID 422560 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH:21]([CH3:26])[C:22]([F:25])([F:24])[F:23])=[N:16][N:15]=[CH:14]2.CN(C(ON1N=NC2[CH:38]=[CH:39][CH:40]=[N:41]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>CN(C)C=O>[CH:40]1([NH:41][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([CH:21]([CH3:26])[C:22]([F:23])([F:24])[F:25])=[N:16][N:15]=[CH:14]4)[CH:4]=2)[CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666754614-Methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoic acid

Product 1

HCID 59726033(+/-) N-Cyclopropyl-4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoic acid (86 mg, 239 μmol) in N,N-dimethylformamide (1000 μl) were added HATU (136 mg, 358 μmol) and cyclopropylamine (8 μl, 2387 μmol). The resulting mixture was stirred at RT for 20 h, during which LC-MS indicated conversion to the desired product. The reaction was diluted with EtOAc and washed with water and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Preparative HPLC purification (Shimadzu) afforded the title compound as a white amorphous solid. MS (ES+): 400.4 (M+H)+.

Sources & evidence

ORD record
ord-ebfa37adafc84f40b2823c91bf62c84d
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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