Sodium Hydroxide → HCID 59427288, compound

HRID 503555Notes

Reaction equation

HRID 503555 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:37]=[CH:36][C:22]([O:23][C:24]4[C:33]5[C:28](=[CH:29][C:30]([C:34]#[N:35])=[CH:31][CH:32]=5)[N:27]=[CH:26][CH:25]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)[CH:7]=1.C(=O)(O)[O-:41].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:37]=[CH:36][C:22]([O:23][C:24]4[C:33]5[C:28](=[CH:29][C:30]([C:34]([NH2:35])=[O:41])=[CH:31][CH:32]=5)[N:27]=[CH:26][CH:25]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67318102HCID 67318102, compound

Product 1

HCID 59427288HCID 59427288, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A sealed tube was charged with 4-(4-(4-(5-fluoro-2-methoxyphenyl)phthalazin-1-ylamino)phenoxy)quinoline-7-carbonitrile (150 mg, 0.529 mmol) in neat concentrated sulfuric acid (3 mL). The tube was sealed and placed in a preheated oil bath at 80° C. for 1 h, at which point the reaction was determined complete by LCMS. The reaction was cooled to RT and added drop-wise to sat. sodium bicarbonate in an ice bath. Neutralized the mixture with 2N NaOH to a pH of 7 and extracted with ethyl acetate (3×). Organic layers were dried over magnesium sulfate, filtered and concentrated. The crude was purified via silica gel chromatography using a slow gradient of 90:10:1 (DCM:methanol:ammonium hydroxide) in DCM. Fractions contained the desired material were pooled and concentrated in vacuo to afford 4-(4-(4-(5-fluoro-2-methoxyphenyl)phthalazin-1-ylamino)phenoxy)quinoline-7-carboxamide as a tan solid. MS m/z=532 [M+H]+. Calc'd for C31H22FN5O3: 531.54.

Workup

  1. customThe tube was sealed
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialOrganic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified via silica gel chromatography
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e68b7bb7a7845379b69a81cdb0bc7bc
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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