Cysteamine → HCID 20634244, compound

HRID 49013Notes

Reaction equation

HRID 49013 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]([CH:21]=O)[C:17]=3[CH:23]=2)[C:3]1=[O:24].[NH2:25][CH2:26][CH2:27][SH:28].C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>O.O1CCCC1.C(O)C>[C:36]([N:25]1[CH2:26][CH2:27][S:28][CH:21]1[C:18]1[C:17]2[CH:23]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:10])([F:11])[F:9])[N:2]([CH3:1])[C:3]3=[O:24])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1)(=[O:38])[CH3:37]

Participants

8

Reactant 4

HCID 6058CysteamineHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Product 1

HCID 20634244HCID 20634244, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.500 g, 1.41 mmol), 2-aminoethanethiol (0.13 g, 1.69 mmol), ethanol and tetrahydrofuran is stirred overnight at room temperature. The mixture is concentrated in vacuo and the residue taken up in methylene chloride. The resultant mixture is treated with triethylamine (0.340 ml, 2.41 mmol), then acetyl chloride (0.120 ml, 1.69 mmol), stirred 90 minutes and poured into water. The resultant mixture is diluted with methylene chloide. The organic layer is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a white solid, which is chromatographed on silica gel with methanol-methylene chloride to afford the title compound as a white solid (0.600 g, 93.3%, mp 135-140° C.) which is identified by NMR spectral analysis.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washThe organic layer is washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo to a white solid, which
  5. customis chromatographed on silica gel with methanol-methylene chloride

Sources & evidence

ORD record
ord-45e532b7e6214a3b89430f8c40f598f1
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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