N,N-Dimethylglycine → HCID 24986176, compound

HRID 642987Notes

Reaction equation

HRID 642987 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[CH3:28][N:29]([CH3:34])[CH2:30][C:31](O)=[O:32].O=P(Cl)(Cl)Cl>CO>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:23])[C:31](=[O:32])[CH2:30][N:29]([CH3:34])[CH3:28])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 19660Carbonate IonHCID 24813Phosphorus oxychlorideHCID 24986173HCID 24986173, compound

Product 1

HCID 24986176HCID 24986176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-N-((1-(4-(methylamino)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (34 mg, 0.1 mmol), prepared as shown in Example 17, was dissolved in 10 mL methanol and treated with MP-carbonate for 1 hr. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in 3 mL pyridine and N,N-dimethylglycine (16 mg, 0.1 mmol) was added. The mixture was then stirred in ice bath. POCl3 (28 μL, 0.3 mmol) was added. The reaction was stirred for 20 min and quenched with methanol. The mixture was concentrated and directly subjected to prep HPLC to isolate the title compound. MS found for C19H21ClN6O2S (M+H)+ 433.1, 435.1 (Cl pattern).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 3 mL pyridine
  4. stirringThe reaction was stirred for 20 min
  5. customquenched with methanol
  6. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-7dbb9789c09d4c15b7b7ad0eb3d9eb58
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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