Dimethylacetamide → HCID 24948156, compound

HRID 1803574Notes

Reaction equation

HRID 1803574 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[N:14]1([C:19]2[CH:20]=[C:21](CN)[CH:22]=[CH:23][CH:24]=2)[CH:18]=[N:17][CH:16]=[N:15]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C[C:80]([N:82](C)C)=O>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:82][CH2:80][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 5

HCID 31374DimethylacetamideHCID 634876Binap, (A+-)-HCID 11378789[3-(1H-1,2,4-Triazol-1-yl)phenyl]methylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948156HCID 24948156, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), [3-(1H-1,2,4-triazol-1-yl)phenyl]methylamine (110 mg, 0.636 mmol), Pd2(dba)3 (53 mg, 0.0578 mmol), rac-BINAP (108 mg, 0.173 mmol) and NaOtBu (246 mg, 2.560 mmol) in DMA (5 mL) was heated at 85° C. for 45 minutes. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(2-[1,2,4]triazol-1-yl-benzylamino)-2H-phthalazin-1-one (24 mg) as a yellow solid, 1H (400 MHz, d6-DMSO) δ: 4.54 (d, 2H), 6.86 (s, 1H), 7.18 (dd, 1H), 7.43 (d, 1H), 7.54 (t, 1H), 7.76 (m, 2H), 7.91 (s, 1H), 7.94 (d, 1H), 8.22 (s, 1H), 9.28 (s, 1H), 12.35 (s, 1H) ppm; m/z (M+1) 352.88.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-21f015d051ba4dc78e047dcdb4cb8c39
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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