Methanesulfonamide → HCID 59520214, compound

HRID 1162580Notes

Reaction equation

HRID 1162580 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:21][C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:17]C(O)=O)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.CC[N:46]([CH:50](C)C)C(C)C.[CH3:53][S:54]([NH2:57])(=[O:56])=[O:55]>CC#N>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:21][C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:17][NH:46][C:50]([NH:57][S:54]([CH3:53])(=[O:56])=[O:55])=[O:34])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11668171HCID 11668171, compound

Product 1

HCID 59520214HCID 59520214, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-{[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-propionic acid (50 mg, 0.14 mmol), diphenyl phosphoryl azide (50 uL, 0.18 mmol) and DIEA (100 μL) was heated in CH3CN at 60° C. for 1 hour. After cooling to room temperature methane sulfonamide (30 mg, 0.32 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 silica gel column (ethyl acetate/hexane 1:1) to afford (2-{[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-ethyl) 3-methanesulfonyl-urea (15 mg). LCMS m/z: 480 (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 silica gel column (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-6ef0293bc78f4806b8b94ac0780e7617
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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