Dimethylamine → HCID 60169087, compound

HRID 1053281Notes

Reaction equation

HRID 1053281 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([C:16](O)=[O:17])=[C:13]([C:19]3[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=3)[C:12]=2[CH3:29])=[CH:7][CH:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([C:16]([N:2]([CH3:3])[CH3:1])=[O:17])=[C:13]([C:19]3[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=3)[C:12]=2[CH3:29])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68285720HCID 68285720, compound2×

Product 1

HCID 60169087HCID 60169087, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

Dimethyl amine (0.055 g, 0.61 ml 2M solution in THF, 1.22 mmol) was added drop wise to a solution of 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 1c, 0.25 g, 0.61 mmol) in dry THF (15 ml) under a nitrogen atmosphere at 0° C. To the reaction mixture HATU (0.26 g, 0.67 mmol) and DIPEA (0.16 g, 0.21 ml, 1.24 mmol) were added at 0° C. with stirring. The mixture was then allowed to warm to 10° C. and stirred for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The concentrated mass so obtained was diluted with ethyl acetate (30 ml) and washed with saturated sodium bicarbonate solution (2×15 ml) and brine (1×15 ml). The organic layer obtained was then dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 25% ethyl acetate in hexanes as an eluent to obtain the title compound (0.06 g, 22.50%).

Workup

  1. stirringstirred for 2 hr
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe concentrated mass so obtained
  4. washwashed with saturated sodium bicarbonate solution (2×15 ml) and brine (1×15 ml)
  5. customThe organic layer obtained
  6. dry with materialwas then dried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-6a05bb4abd574ebcbc2584551ba76424
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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