Methanesulfonyl chloride → HCID 22046315, compound

HRID 1821730Notes

Reaction equation

HRID 1821730 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)=[O:10])[CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:19][O:18][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:7][C:6]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 220462781-(5-Amino-2-methoxyphenyl)-3-pyrazin-2-yl-urea2×

Product 1

HCID 22046315HCID 22046315, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(5-amino-2-methoxyphenyl)-3-pyrazin-2-yl-urea (Compound 14, Example 4) (260 mg, 1 mmol) in dry pyridine (15 mL) was treated with methanesulfonyl chloride (0.08 mL, 1 mmol) and stirred 16 h at room temperature. The reaction mixture was concentrated in vacuo and the solid residue was triturated with ethanol, collected by filtration, and dried in vacuo to afford the product (205 mg, 61%). 1H NMR (300 Mhz, d6-DMSO) δ: 10.16 (s, 1H), 10.07 (s, 1H), 9.40 (s, 1H), 8.92 (s, 1H), 8.35 (s, 1H), 8.27 (s, 1H), 8.19 (d, J=2.2 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H), 6.91 (dd, J=8.7, 2.4 Hz, 1H), 3.91 (s, 3H), 2.91 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe solid residue was triturated with ethanol
  3. filtrationcollected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-914a818c82584736bd9970f4570f17d4
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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