Methanesulfonamide → HCID 59520217, compound

HRID 1162579Notes

Reaction equation

HRID 1162579 reaction equation
[CH:1]1([N:6]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[N:16]=2)[CH2:7][CH2:8]C(O)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.CC[N:45]([CH:49](C)C)C(C)C.[CH3:52][S:53]([NH2:56])(=[O:55])=[O:54]>CC#N>[CH:1]1([N:6]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH:23]([CH3:24])[CH3:25])=[CH:21][CH:22]=3)[N:16]=2)[CH2:7][CH2:8][NH:45][C:49]([NH:56][S:53]([CH3:52])(=[O:55])=[O:54])=[O:33])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11717424HCID 11717424, compound

Product 1

HCID 59520217HCID 59520217, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-{cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-propionic acid (100 mg, 0.28 mmol), diphenyl phosphoryl azide (70 ul, 0.25 mmol) and DIEA (150 μl) was heated in CH3CN at 60° C. for 1 hour. After cooling to room temperature methane sulfonamide (50 mg, 0.52 mmol) was added and reaction mixture was stirred. After 16 h, the reaction mixture was concentrated in high vacuum. The crude residue was purified on a silica gel column (ethyl acetate/hexane 1:1) to afford 1-(2-{cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-ethyl)-3-methanesulfonyl-urea (25 mg). LCMS m/z: 452 (M+1)+.

Workup

  1. additionwas added
  2. customreaction mixture
  3. concentrationthe reaction mixture was concentrated in high vacuum
  4. customThe crude residue was purified on a silica gel column (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-d3aa1b6aabf7458f90ffa0856e027e06
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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