Lithium Hydroxide → HCID 57500641, compound

HRID 1919634Notes

Reaction equation

HRID 1919634 reaction equation
CS([C:5]1[N:6]=[CH:7][C:8]2[C:17]3[CH:16]=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][C:12]=3[N:11]=[C:10]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]=2[N:29]=1)(=O)=O.Cl.CN.C[CH2:34][N:35](C(C)C)C(C)C.[Li+].[OH-]>CN(C=O)C.O.CO.C1COCC1>[CH3:34][NH:35][C:5]1[N:6]=[CH:7][C:8]2[C:17]3[CH:16]=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[N:11]=[C:10]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]=2[N:29]=1

Participants

9

Reactant 4

HCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 57500647HCID 57500647, compound

Product 1

HCID 57500641HCID 57500641, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a closed vial, methyl 3-(methylsulfonyl)-5-(phenylamino)pyrimido[4,5-c]quinoline-8-carboxylate (1.0 eq, 62 mg, 0.152 mmol) was mixed with Methylamine hydrochloride (100 mg), DIEA (260 ul) in DMF (1 ml). The mixture was stirred at 60° C. for 40 min. Addition of water induced precipitation of methyl 3-(methylamino)-5-(phenylamino)pyrimido[4,5-c]quinoline-8-carboxylate which was isolated by filtration. This material was suspended in a 1:1:1 mixture of THF, MeOH and water (4 ml), and vigorously stirred at 60° C. in the presence of LiOH (200 mg) for 1.5 hours. Water aqueous HCl were added and to reach pH=1. The solid was filtered, dried and triturated in AcOEt/hexanes to provide 3-(methylamino)-5-(phenylamino)pyrimido[4,5-c]quinoline-8-carboxylic acid as a yellow solid (40 mg, 74% yield). LCMS (ES): >95% pure, m/z 346 [M+1]+.

Workup

  1. customprecipitation of methyl 3-(methylamino)-5-(phenylamino)pyrimido[4,5-c]quinoline-8-carboxylate which
  2. customwas isolated by filtration
  3. filtrationThe solid was filtered
  4. customdried
  5. customtriturated in AcOEt/hexanes

Sources & evidence

ORD record
ord-ded88322a0c44113ba5a7b12a95826e5
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…