4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 66816522, compound

HRID 1755047Notes

Reaction equation

HRID 1755047 reaction equation
C[N+]1([C:8]2[N:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([O:16][CH3:17])[N:9]=2)CCOCC1.[Cl-].[CH:19]1([C:25]2[NH:29][C:28](=[O:30])[C:27]3([CH2:35][CH2:34][N:33]([S:36](/[CH:39]=[CH:40]/[C:41]4[C:49]([CH3:50])=[CH:48][C:44]([C:45]([OH:47])=[O:46])=[CH:43][C:42]=4[CH3:51])(=[O:38])=[O:37])[CH2:32][CH2:31]3)[N:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[CH3:17][O:16][C:10]1[N:11]=[C:12]([O:14][CH3:15])[N:13]=[C:8]([O:46][C:45](=[O:47])[C:44]2[CH:48]=[C:49]([CH3:50])[C:41](/[CH:40]=[CH:39]/[S:36]([N:33]3[CH2:32][CH2:31][C:27]4([N:26]=[C:25]([CH:19]5[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]5)[NH:29][C:28]4=[O:30])[CH2:35][CH2:34]3)(=[O:37])=[O:38])=[C:42]([CH3:51])[CH:43]=2)[N:9]=1

Participants

4

Reactant 2

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 66818434HCID 66818434, compound

Product 1

HCID 66816522HCID 66816522, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

DMT-MM (181 mg, 0.50 mmol) was added to a solution of 4-[(E)-2-(2-cyclohexyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-vinyl]-3,5-dimethyl-benzoic acid (160 mg, 0.33 mmol) in anhydrous ethanol (3.3 ml), and the mixture was stirred at room temperature for 15 hours. The mixture was concentrated under reduced pressure, and the resulting residue was then purified by silica gel column chromatography (dichloromethane-methanol) to give 4-[(E)-2-(2-cyclohexyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-vinyl]-3,5-dimethyl-benzoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester (109 mg, 53%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was then purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-3737c232e58146648a90999fda59c33c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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