Water → HCID 178434789, compound

HRID 2246292Notes

Reaction equation

HRID 2246292 reaction equation
[SH:1][C:2]1[NH:6][CH:5]=[N:4][N:3]=1.Cl[C:8]1[CH:9]=[CH:10][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]3[S:23][N:22]=[C:21]([CH3:24])[N:20]=3)[C:16]=2[N:17]=1.C(O[K])(C)(C)C.O>CN(C)C(=O)C>[N:4]1[N:3]=[C:2]([S:1][C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]4[S:23][N:22]=[C:21]([CH3:24])[N:20]=4)[C:16]=3[N:17]=2)[NH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 23160294(6-Chloro-pyrido[3,2-d]pyrimidin-4-yl)-3-methyl-[1,2,4]thiadiazol-5-yl-amineHCID 178418922HCID 178418922, compoundHCID 178527972HCID 178527972, compound

Product 1

HCID 178434789HCID 178434789, compoundYield 2.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

3-Mercapto-4H-[1,2,4]triazole (54 mg; 0.54 mmol) and 100 mg (0.36 mmol) of (6-chloro-pyrido[3,2-d]pyrimidin-4-yl)-3-methyl-[1,2,4]thiadiazol-5-yl-amine were added to a solution of 80 mg (0.72 mmol) of tert-butoxy potassium in 3 ml of N,N-dimethylacetamide and the mixture was stirred at 130° C. for 16 hours. Water was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90) to give 3 mg (yield: 2%) of the title compound as a yellow solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90)

Sources & evidence

ORD record
ord-9e2d96fd6e9d44998cdf65a2f93b4a92
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

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