Methanesulfonic Acid → HCID 178505341, compound

HRID 1518163Notes

Reaction equation

HRID 1518163 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH2:15][C:14]4([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[O:13][N:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:31])([F:30])[F:29])[CH:3]=1.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>CCOC(C)=O>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[Cl:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH2:15][C:14]4([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[O:13][N:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:29])([F:30])[F:31])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178506370HCID 178506370, compound

Product 1

HCID 178505341HCID 178505341, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[7-Chloro-5-(2-trifluoromethoxyphenyl)-1H-benzimidazol-2-yl]-1-oxa-2-aza-spiro[4.5]dec-2-ene (64.0 mg, 0.142 mmol, as prepared in the previous step) was placed in an 8 mL vial, and EtOAc (1 mL) was added. Methanesulfonic acid (9.22 μL, 0.142 mmol) was added via microsyringe. The solvent was removed under reduced pressure. The residue was triturated with ether (4 mL), and the solvent was removed via pipette. Trituration and solvent removal were repeated. The solid was dried under high vacuum to yield 72.3 mg (93%) of the title compound. 1H-NMR (400 MHz, d6-DMSO) δ: 7.59-7.66 (m, 1H), 7.45-7.59 (m, 4H), 7.40 (s, 1H), 3.32 (s, 2H), 2.33 (s, 3H), 1.59-1.82 (m, 6H), 1.30-1.59 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C23H19ClF3N3O2: 450.1 (M+H). found: 450.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with ether (4 mL)
  3. customthe solvent was removed via pipette
  4. customTrituration and solvent removal
  5. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-915c21424f944cecb38bebf638ec4a63
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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