Sulfamide → HCID 70663176, compound

HRID 878300Notes

Reaction equation

HRID 878300 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:8]([N:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[O:25][CH3:26])[CH3:11])=[O:9].[S:34](N)([NH2:37])(=[O:36])=[O:35]>C(OC(=O)C)(C)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:10]([CH3:11])[C:8](=[O:9])[C:7]2[CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:29]=[C:5]([S:4][CH2:3][CH2:2][NH:1][S:34](=[O:36])(=[O:35])[NH2:37])[CH:6]=2)=[C:19]([O:25][CH3:26])[CH:20]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 70663436HCID 70663436, compound

Product 1

HCID 70663176HCID 70663176, compound

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

To a solution of 3-(2-aminoethylthio)-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide (0.1 g, 209 μmol, example 237) in isopropylacetate (2 mL) was added sulfamide (80.2 mg, 834 μmol) and the mixture was heated at reflux for 23 hours while the solvent was vaporized. The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless foam (0.067 g; 57%). MS (ESI): m/z=559.11 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 23 hours while the solvent
  3. customThe product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-c5945df888a84a6d9cafef55b59ce53f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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