Dimethyl Sulfoxide → HCID 22386456, compound

HRID 1072551Notes

Reaction equation

HRID 1072551 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[N:8][N:7]=1.CS(C)=[O:29]>CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[O:29])=[N:8][N:7]=1

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 6918616N-(3-bromo-4-methylphenyl)-4-(pyridin-4-ylmethyl)phthalazin-1-amine

Product 1

HCID 22386456HCID 22386456, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.22 g (3 mmol) 1-(3-brom-4-methyl-anilino)-4-(4-pyridyl-methyl)-phthalazine (expl. 14h) and 336 mg (3 mmol) potassium-tert.butylate in 10 ml DMSO is stirred in an open vessel for 10 days at RT. Then the yellow mixture is diluted with EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and partly concentrated. After adding 10 g of SiO2, the residue is dried in vacuo and the resulting powder put on top of a SiO2-column. Eluation with dichloromethane/EtOAc (5:1→1:1→EtOAc) yields [4-(3-brom-4-methylanilino)phthalazin-1-yl](pyridin-4-yl)ketone (A) followed by [4-(3-brom-4-methylanilino)phthalazin-1-yl](pyridin-4-yl)methanol (B). A: m.p. 249-250° C.; FAB MS (M+H)+=419/421. B: m.p. 240° C.; FAB MS (M+H)+=421/423.

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed twice with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationpartly concentrated
  6. additionAfter adding 10 g of SiO2
  7. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-9129378c0cf64dcc8687db3af740951a
Source dataset
uspto-grants-2005_06
Patent number
US06911440B2

Reaction notes

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