Thionyl Chloride → HCID 59427296, compound

HRID 1013757Notes

Reaction equation

HRID 1013757 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-487a662cc499431b9ebf2490c78c758c
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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