Sulfamide → HCID 60196697, compound

HRID 878331Notes

Reaction equation

HRID 878331 reaction equation
[NH:1]1[CH2:4][CH:3]([S:5]([C:8]2[CH:9]=[C:10]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=2)[C:11]([N:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[O:28][CH3:29])[CH3:14])=[O:12])(=[O:7])=[O:6])[CH2:2]1.[S:37](=[O:41])(=[O:40])(N)[NH2:38]>C(OC(=O)C)(C)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[N:13]([CH3:14])[C:11](=[O:12])[C:10]2[CH:30]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:32]=[C:8]([S:5]([CH:3]3[CH2:4][N:1]([S:37](=[O:41])(=[O:40])[NH2:38])[CH2:2]3)(=[O:7])=[O:6])[CH:9]=2)=[C:22]([O:28][CH3:29])[CH:23]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 70663236HCID 70663236, compound

Product 1

HCID 60196697HCID 60196697, compound

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

A suspension of 3-(azetidin-3-ylsulfonyl)-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide (0.05 g, 95.5 μmol, example 280) and sulfuric diamide (36.7 mg, 382 μmol) in isopropylacetate (1 mL) was heated at reflux for 19 hours. The reaction mixture was evaporated and the product purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Light brown solid (0.035 g; 60%). MS (ESI): m/z=603.10 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hours
  3. customThe reaction mixture was evaporated
  4. customthe product purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-4dde9aec18da4f2aa66868c1352932c5
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…