Hydrochloric Acid → HCID 178478956, compound

HRID 1518141Notes

Reaction equation

HRID 1518141 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[C:11]2[NH:12][C:13]([C:15]3[CH2:19][C:18]4([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[O:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1.Cl>CCOC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[C:11]2[NH:12][C:13]([C:15]3[CH2:19][C:18]4([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]4)[O:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178506071HCID 178506071, compound

Product 1

HCID 178478956HCID 178478956, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[5-(2-Chloro-phenyl)-7-trifluoromethyl-1H-benzimidazol-2-yl]-1-oxa-2-aza-spiro[4.5]dec-2-ene (1.14 g, 2.63 mmol, as prepared in the previous step) was placed in a 100 mL round-bottom flask, and EtOAc (10 mL) was added. HCl (1 eq., 2.60 mL, 2.63 mmol, 1 M solution in ether) was added via syringe. The solvent was removed under reduced pressure, and the solid was dried under high vacuum for 3 days, yielding 1.12 g (90%) of the desired compound. 1H-NMR (400 MHz, d6-DMSO) δ: 7.80 (s, 1H), 7.60-7.66 (m, 1H), 7.59 (s, 1H), 7.52-7.58 (m, 1H), 7.43-7.51 (m, 2H), 1.61-1.82 (m, 6H), 1.32-1.59 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H19ClF3N3O: 434.1 (M+H). found: 434.2.

Workup

  1. customwas placed in a 100 mL round-bottom flask
  2. customThe solvent was removed under reduced pressure
  3. customthe solid was dried under high vacuum for 3 days

Sources & evidence

ORD record
ord-c072796e4654432eaf5d9ebcbcf621ff
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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