Ammonia → HCID 22741970, compound

HRID 49907Notes

Reaction equation

HRID 49907 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[N:15][N:14]=1.N.ClCCl>CN1C(=O)N(C)CC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[N:15][N:14]=2)=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 4592964'-Amino-2'-hydroxyacetophenoneHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 22741970HCID 22741970, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

302 mg (2.0 mmol) 2-acetyl-5-aminophenol (Maybridge) and 256 mg (1.00 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine (Example 67A.1) in 2 ml DMEU are heated for 3-18 h to 100° C. The reaction mixture is stirred with 10 ml NH3 solution (10% in water) and 25 ml ethyl actetate (or dichloromethane) and filtered via Celite. The organic phase of the filtrate is dried (Na2SO4), evaporated, and chromatographed (SiO2; ethyl acetate/CH3OH, 40:1→10:1) Crystallization from acetonitrile yields the title compound: m.p.: 234-236° C.; HPLC: tRet(Grad5-40)=9.5; FAB MS (M+H)+=371.

Workup

  1. customare heated for 3-18 h to 100° C
  2. filtrationfiltered via Celite
  3. dry with materialThe organic phase of the filtrate is dried (Na2SO4)
  4. customevaporated
  5. customchromatographed
  6. custom(SiO2; ethyl acetate/CH3OH, 40:1→10:1) Crystallization from acetonitrile

Sources & evidence

ORD record
ord-7fa2b68b71ce456ab707c8716c273d45
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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