Dimethylacetamide → Alvelestat

HRID 1888830Notes

Reaction equation

HRID 1888830 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:26][S:27]([C:30]1[CH:31]=[CH:32][C:33]([CH2:36][NH2:37])=[N:34][CH:35]=1)(=[O:29])=[O:28].[CH3:38][C:39]1[N:44]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)[C:43](=[O:55])[C:42]([C:56](O)=[O:57])=[CH:41][C:40]=1[C:59]1[N:60]([CH3:64])[N:61]=[CH:62][CH:63]=1.CC(N(C)C)=O>CN1C(=O)CCC1>[CH3:38][C:39]1[N:44]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:52])[F:53])[CH:46]=2)[C:43](=[O:55])[C:42]([C:56]([NH:37][CH2:36][C:33]2[CH:32]=[CH:31][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:35][N:34]=2)=[O:57])=[CH:41][C:40]=1[C:59]1[N:60]([CH3:64])[N:61]=[CH:62][CH:63]=1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594558756-Methyl-5-(1-methyl-1H-pyrazol-5-yl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acidHCID 66725223[5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride

Product 1

HCID 46861623AlvelestatYield 20.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

HBTU (30 mg, 0.079 mmol) was added to {[5-(methylsulfonyl)pyridin-2-yl]methyl}amine hydrochloride (20 mg, 0.090 mmol), 6-methyl-5-(2-methyl-2H-pyrazol-3-yl)-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid (Example 92 (a), 27 mg, 0.072 mmol) and DMA (23 μl, 0.31 mmol) in NMP (0.25 ml) and the mixture was stirred in a sealed vial overnight. The product was purified by preparative HPLC and freeze-dried to give the title compound as a white solid (8 mg, 20%).

Workup

  1. customThe product was purified by preparative HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-8ae898f73f294ced88c8b6e90956db7e
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

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