Methanesulfonic Acid → HCID 24762958, compound

HRID 556384Notes

Reaction equation

HRID 556384 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[C:26]([CH2:28][O:29]CC5C=CC=CC=5)[N:25]=[CH:24][N:23]=4)=[CH:20][C:15]=3[O:14][CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.CS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[F:37][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[C:26]([CH2:28][OH:29])[N:25]=[CH:24][N:23]=4)=[CH:20][C:15]=3[O:14][CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 24762957HCID 24762957, compound

Product 1

HCID 24762958HCID 24762958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 133 mg (0.256 mMol) 6-(6-benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide in 13.3 ml CH2Cl2 is cooled in an icebath. 3.3 ml H3CSO3H are added and stirring is continued for 2.5 h at rt. The solution is poured into a vigorousely stirred mixture of 70 g ice and 70 ml sat. Na2CO3 solution. After 5 min, the mixture is extracted 3 times with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; EtOAc/hexane 1:19→1:1→EtOAc) gives the title compound: m.p.: 181-182° C.; MS: [M+1]+=430; Anal.: C,H,N,F; 1H MNR (DMSO-d6): δ ppm 10.56 (s, HN), 8.85 (s, 1H), 8.65 (s, 1H), 8.22 (s, 1H), 8.15 (d, 1H), 8.01 (d, 1H), 7.72 (s, 1H), 7.63 (t, 1H), 7.47 (d, 1H), 7.27 (d, 1H), 7.06 (s, 1H), 5.67 (sb, HO), 4.55 (s, CH2).

Workup

  1. waitAfter 5 min
  2. extractionthe mixture is extracted 3 times with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20a17ff647f644349851ce3744b7ff46
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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