Lithium Hydroxide → HCID 68183192, compound

HRID 513701Notes

Reaction equation

HRID 513701 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:30])[C:6]1[CH:11]=[C:10]([CH:12]2[C:25]3[CH:24]=[CH:23][C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[NH:15][S:14](=[O:27])(=[O:26])[N:13]2[CH3:28])[CH:9]=[CH:8][C:7]=1[F:29]>O.C1COCC1.CO>[F:29][C:7]1[CH:8]=[CH:9][C:10]([CH:12]2[C:25]3[CH:24]=[CH:23][C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[NH:15][S:14](=[O:27])(=[O:26])[N:13]2[CH3:28])=[CH:11][C:6]=1[C:5]([OH:30])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68183006HCID 68183006, compound

Product 1

HCID 68183192HCID 68183192, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH (10 mg, 0.25 mmol) in water (0.5 ml) was added to a solution of 2-fluoro-5-(2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3λ*6*-thia-2,4,5-triaza-phenanthren-1-yl)-benzoic acid methyl ester 423 (50 mg, 0.12 mmol) in THF:MeOH (1:1; 2 ml) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo, the residue was diluted in the minimum amount of water and acidified to pH=3-4 with 2 M HCl. The resulting precipitate was collected by filtration and dried. The crude solid was purified by preparative HPLC (acidic conditions 1) to give the title compound (8 mg, 17%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted in the minimum amount of water
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried
  5. customThe crude solid was purified by preparative HPLC (acidic conditions 1)

Sources & evidence

ORD record
ord-60255a85d88242c397d41fca615bf15b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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