4-Methylsulfonylbenzylamine hydrochloride → 5-Iodo-1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

HRID 524336Notes

Reaction equation

HRID 524336 reaction equation
Br[C:2]1[C:3](=[O:15])[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]([CH:9]([CH3:11])C)[C:7]=1[CH3:8].[I:16]C1C(=O)C(C(O)=O)=CN(CCOC)C=1C.Cl.CS(C1C=CC(CN)=CC=1)(=O)=O.[CH3:45][S:46]([C:49]1[CH:50]=[CH:51][C:52]([CH2:55][NH2:56])=[N:53][CH:54]=1)(=[O:48])=[O:47].CN([C:60]([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[CH3:45][S:46]([C:49]1[CH:50]=[CH:51][C:52]([CH2:55][NH:56][C:12]([C:4]2[C:3](=[O:15])[C:2]([I:16])=[C:7]([CH3:8])[N:6]([CH2:9][CH2:11][O:64][CH3:60])[CH:5]=2)=[O:14])=[N:53][CH:54]=1)(=[O:48])=[O:47]

Participants

7

Reactant 6

HCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57354332(5-(Methylsulfonyl)pyridin-2-yl)methanamineHCID 867115775-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidHCID 867115795-Iodo-1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Product 1

HCID 867115875-Iodo-1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

Procedure

Preparation 22 is prepared following the procedure for preparation 5, substituting preparation 3c with preparation 13b, 4-methylsulfonylbenzylamine hydrochloride with C-(5-methanesulfonyl-pyridin-2-yl)-methylamine and HBTU with TBTU. ESI mass spectrum: [M+H]+=506; Retention time HPLC: 0.90 min (Z003_003).

Workup

  1. customPreparation 22
  2. customis prepared
  3. customfor preparation 5

Sources & evidence

ORD record
ord-7eb9f60514894f70aab724f1704a2a2d
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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