2-Dimethylaminopyridine → HCID 22119832, compound

HRID 1274646Notes

Reaction equation

HRID 1274646 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].C(Cl)(=O)C(Cl)=O.C(N[N:39](NC(C)C)[SH:40](=[O:42])=[O:41])(C)C.C([N:49]([CH:53]([CH3:55])[CH3:54])[CH:50]([CH3:52])[CH3:51])C.CN(C1C=CC=CN=1)C>CN(C)C=O.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22]([NH:39][S:40](=[O:42])(=[O:41])[N:49]([CH:53]([CH3:55])[CH3:54])[CH:50]([CH3:52])[CH3:51])=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28]

Participants

8

Reactant 5

HCID 218852-DimethylaminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 22119820HCID 22119820, compoundHCID 178458065HCID 178458065, compound

Product 1

HCID 22119832HCID 22119832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-dimethylformamide (8 drops) is added to a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-α,α-dimethyl-1,2-benzisothiazole-3-acetic acid (0.800 g, 0.00194 mol) and methylene chloride. The mixture is cooled on an ice bath and oxalyl chloride (2.0 M in methylene chloride, 2.42 ml, 0.00485 mol) is added. The resultant mixture is stirred one hour on an ice bath and concentrated in vacuo. The residue is taken up in tetrahydrofuran. N,N-Diisopropylaminosulfonamide (0.410 g, 0.00278 mol), ethyldiisopropylamine (0.310 g, 0.00240 mol) and dimethylaminopyridine (0.0100 g) are added and the resultant mixture is stirred overnight at room temperature. The mixture is then filtered and the filtrate is concentrated in vacuo to afford a yellow resin. The resin is filtered through silica gel to afford the title compound as a tan resin (0.500 g, 44.8%).

Workup

  1. temperatureThe mixture is cooled on an ice bath
  2. concentrationconcentrated in vacuo
  3. filtrationThe mixture is then filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto afford a yellow resin
  6. filtrationThe resin is filtered through silica gel

Sources & evidence

ORD record
ord-dc50dde70bab4309bdb77e33ab17a82a
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

Loading…