Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 5-Ethynyl-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 1802612Notes

Reaction equation

HRID 1802612 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)#[CH:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:35][CH2:36][C:37]1[N:38]=[CH:39][N:40]([C:42]2[CH:47]=[CH:46][C:45]([N:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]3=[O:54])=[CH:44][CH:43]=2)[CH:41]=1>CN(C=O)C>[C:1]([C:3]1[S:7][C:6]([C:8]([NH:35][CH2:36][C:37]2[N:38]=[CH:39][N:40]([C:42]3[CH:43]=[CH:44][C:45]([N:48]4[CH:53]=[CH:52][CH:51]=[CH:50][C:49]4=[O:54])=[CH:46][CH:47]=3)[CH:41]=2)=[O:10])=[CH:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 450847505-Ethynylthiophene-2-carboxylic acidHCID 669741021-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

Product 1

HCID 247604525-Ethynyl-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-ethynyl-thiophene-2-carboxylic acid (83 mg, 0.54 mmol) and TEA (0.15 mL, 1.1 mmol) in DMF (4 mL), HATU (228 mg, 0.60 mmol) was added. After being stirred at room temperature for 30 min, a solution of 1-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one prepared above (145 mg, 0.54 mmol) and TEA (0.15 mL, 1.1 mmol) in DMF (8 mL) was added. The mixture was stirred at room temperature overnight. It was then purified by HPLC to give the title compound (65 mg). MS 401 (M+H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature overnight
  3. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-36954799203b4677a82edf2190e5b0d2
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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