Hydrochloric Acid → HCID 178478960, compound

HRID 1518115Notes

Reaction equation

HRID 1518115 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[C:8]2[NH:9][C:10]([C:12]3[CH2:16][C:15]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[O:14][N:13]=3)=[N:11][C:7]=2[CH:6]=[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH:4]=1.CO.[ClH:36]>CCOCC>[ClH:36].[F:33][C:2]([F:1])([F:32])[C:3]1[C:8]2[NH:9][C:10]([C:12]3[CH2:16][C:15]4([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[O:14][N:13]=3)=[N:11][C:7]=2[CH:6]=[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178506131HCID 178506131, compound

Product 1

HCID 178478960HCID 178478960, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-[7-Trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-benzimidazol-2-yl]-1-oxa-2-aza-spiro[4.5]dec-2-ene (524 mg, 1.12 mmol, as prepared in the previous step) was placed in an 8 mL vial, dry MeOH (2 mL) was added, and the mixture was warmed until the solid dissolved. This mixture was added to a mL vial containing ether (20 mL) and 1 M HCl in ether (1.12 mL, 1.12 mmol), resulting in a homogeneous solution. The solution was transferred to a 100 mL round-bottom flask, the solvent was removed under reduced pressure, and the solid was dried under vacuum, giving 469 mg (83%) of the desired HCl salt. 1H-NMR (400 MHz, d6-DMSO) δ: 7.89 (d, J=7.6 Hz, 1H), 7.73-7.81 (m, 1H), 7.71 (s, 1H), 7.63-7.70 (m, 1H), 7.55 (d, J=7.3 Hz, 1H), 7.48 (s, 1H), 3.33 (s, 2H), 1.62-1.83 (m, 6H), 1.33-1.59 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C23H19F6N3O: 468.1 (M+H). found: 468.3. Elemental Analysis Calcd. for C23H19F6N3O: C, 59.10; H, 4.10; F, 24.39; N, 8.99. Found C, 59.06; H, 4.04; F, 24.30; N, 9.04 (% H2O 0.39, Pd <1 ppm).

Workup

  1. temperaturethe mixture was warmed until the solid
  2. dissolutiondissolved
  3. additionThis mixture was added to a mL vial
  4. customresulting in a homogeneous solution
  5. customThe solution was transferred to a 100 mL round-bottom flask
  6. customthe solvent was removed under reduced pressure
  7. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-769e63efddaf42b68b5c880bba304b9f
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

Loading…