Thionyl Chloride → HCID 59427296, compound

HRID 1042898Notes

Reaction equation

HRID 1042898 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:37]([NH2:39])=O.S(Cl)(Cl)=O>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[N:23][N:22]=4)=[CH:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:37]#[N:39]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67318188HCID 67318188, compound

Product 1

HCID 59427296HCID 59427296, compound

Conditions

Temperature
80 °C

Procedure

7-Methoxy-4-(4-(4-phenylphthalazin-1-ylamino)phenoxy)quinoline-6-carboxamide (125 mg, 243 μmol) and thionyl chloride (10 ml, 24341 μmol) were combined and heated to 80° C. for 3 hours. Thionyl chloride was then removed under vacuum. The mixture was then made basic with sat. sodium bicarbonate and extracted with DCM. The organic extracts were combined, dried with sodium sulfate, filtered and concentrated. The product was purified by silica gel chromatography using a 0 to 70% gradient of 90/10/1 (DCM/methanol/ammonium hydroxide) in DCM. MS: M+H+=496.

Workup

  1. customThionyl chloride was then removed under vacuum
  2. extractionextracted with DCM
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dc59a66e847d4ed982e5e871af9c3489
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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