Thiomorpholine 1,1-dioxide → HCID 25211192, compound

HRID 1409806Notes

Reaction equation

HRID 1409806 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[NH:19]1[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]1>>[O:25]=[S:22]1(=[O:26])[CH2:23][CH2:24][N:19]([C:16]([C:14]2[S:15][C:11]([C:3]3[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=3)=[CH:12][CH:13]=2)=[O:18])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 25211192HCID 25211192, compoundYield 80%

Procedure

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and thiomopholine 1,1-dioxide by the method described in Example 2 Method B. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a 1 N aqueous hydrochloric acid solution followed by water. The solid was air dried to afford product as a colorless solid (157 mg, 80%). 1H NMR (DMSO-d6) 2.34 (d, J=1.7, 3 H), 3.27 (obs m, 4 H), 4.00 (m, 4 H), 7.58 (d, J=3.5, 1 H), 7.68 (d, J=4.0, 1 H). 13C NMR (incomplete, F-coupled carbons obscured by baseline noise due to poor solubility) 8.0, ˜44 (br), 51.5, 116.6, 128.0, 130.0, 130.8, 139.6, 158.5, 162.7. 19F NMR −62.2. LC/MS 5.80 min, [M+1]+ 395.

Workup

  1. customThe reaction mixture was evaporated to a solid
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. washwashed with a 1 N aqueous hydrochloric acid solution
  5. customdried

Sources & evidence

ORD record
ord-fbfede59a1204dfa904c8bcdd8c9fe46
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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