Methanol--water (1/1) → HCID 59427324, compound

HRID 1042901Notes

Reaction equation

HRID 1042901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:24]=[CH:23][C:22]([O:25][C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][N:34]=5)[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)=[CH:4][C:3]=1[O:38][CH2:39][CH2:40]SC.O[O:44][S:45]([O-:47])=O.[K+].[CH3:49]O.O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:24]=[CH:23][C:22]([O:25][C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][N:34]=5)[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)=[CH:4][C:3]=1[O:38][CH2:39][CH2:40][S:45]([CH3:49])(=[O:47])=[O:44]

Participants

4

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 67318061HCID 67318061, compound

Product 1

HCID 59427324HCID 59427324, compound

Procedure

4-(4-Chloro-3-(2-(methylthio)ethoxy)phenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine (150 mg, 252 μmol) and oxone (464 mg, 755 μmol) were combined in 3:1 MeOH/water (20 ml) and stirred for 3 h. The mixture was then concentrated to remove methanol, then extracted with DCM, dried with sat. sodium bicarb., and concentrated. The crude material was then purified by chromatography using 0 to 100% 90/10/1 in DCM, followed by reverse phase chromatography to provide the titled compound. MS: M+H+=628.

Workup

  1. concentrationThe mixture was then concentrated
  2. customto remove methanol
  3. extractionextracted with DCM
  4. dry with materialdried with sat. sodium bicarb
  5. concentration, and concentrated
  6. customThe crude material was then purified by chromatography

Sources & evidence

ORD record
ord-ecfd0c8024f44bc88360850adf213421
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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