Dimethylformamide → HCID 89767712, compound

HRID 591513Notes

Reaction equation

HRID 591513 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([O:5][C:6]1[CH:7]=[C:8]2[S:12][CH:11]=[C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:9]2=[C:18]([C:20](O)=[O:21])[CH:19]=1)=[O:4].[CH3:25][N:26](C=O)[CH3:27].Cl.CNC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O>[C:3]([O:5][C:6]1[CH:19]=[C:18]([C:20](=[O:21])[N:26]([CH3:27])[CH3:25])[C:9]2[C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][S:12][C:8]=2[CH:7]=1)(=[O:4])[C:2]([CH3:24])([CH3:23])[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118656069HCID 118656069, compound

Product 1

HCID 89767712HCID 89767712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-((2,2-dimethylpropanoyl)oxy)-3-(2-methoxy-2-oxoethyl)-1-benzothiophene-4-carboxylic acid (145 mg) and DMF (dry) (5 mL) were added dimethylamine hydrochloride (50.6 mg), TEA (0.115 mL) and HATU (236 mg) at room temperature. The mixture was stirred at room temperature for 4 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (133 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-b3db6e020b864670aee5c4512e96a60e
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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