Benzoyl chloride → HCID 25226574, compound

HRID 1514371Notes

Reaction equation

HRID 1514371 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]3[CH3:20])=[C:10]3[CH:21]=[N:22][CH:23]=[CH:24][C:9]=23)=[C:4]([F:25])[CH:3]=1.CCN(C(C)C)C(C)C.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CCCCCC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:42])[CH2:16][C@H:15]3[CH3:20])=[C:10]3[CH:21]=[N:22][CH:23]=[CH:24][C:9]=23)=[C:4]([F:25])[CH:3]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 57657607HCID 57657607, compound

Product 1

HCID 25226574HCID 25226574, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-(4-chloro-2-fluorophenyl)-4-((R)-2-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine (118 mg, 330 μmol) was dissolved in Hünig's base 13 (0.200 ml, 1148 μmol) and DMF (2 ml). Benzoyl chloride (0.0478 ml, 412 μmol) was added and the solution stirred at RT for 2 days. The reaction was then taken up in ethyl acetate (30 ml) and washed with aqueous K2CO3 (10%), water, and brine. The organic phase was dried (MgSO4) and evaporated to give an orange oil. Chromatography of the residue over silica with a gradient of hexane to 100% ethyl acetate gave ((R)-4-(1-(4-chloro-2-fluorophenyl)pyrido[3,4-d]pyridazin-4-yl)-3-methylpiperazin-1-yl)(phenyl)methanone 14 as a yellow solid. LC/MS m/z=462 (M+H+).

Workup

  1. washwashed with aqueous K2CO3 (10%), water, and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give an orange oil

Sources & evidence

ORD record
ord-d84acf48c22c46b9bb6f50aa07cde800
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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