Hydrochloric Acid → HCID 86281552, compound

HRID 510225Notes

Reaction equation

HRID 510225 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:23][CH2:22][C:21]2[C:20]([C:24]3[N:28](C4CCCCO4)[N:27]=[CH:26][CH:25]=3)=[N:19][CH:18]=[N:17][C:16]=2[CH2:15]1)=[O:13].Cl.[OH-].[Na+]>CO.O>[NH:28]1[C:24]([C:20]2[C:21]3[CH2:22][CH2:23][N:14]([C:12]([C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:10])([F:9])[F:11])[C:2]=4[Cl:1])=[O:13])[CH2:15][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:25][CH:26]=[N:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90407753HCID 90407753, compound

Product 1

HCID 86281552HCID 86281552, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Example 17 (224 mg, 0.46 mmol) in MeOH (2 mL) was added 6 M HCl (0.30 mL). The mixture was aged for 3 h and then neutralized with solid NaOH (74 mg, 1.84 mmol) dissolved in a minimum amount of water. The mixture was then concentrated in vacuo. The material was dissolved in DCM and stirred overnight. Filtration removed the inorganic solids and the filtrate was concentrated in vacuo. Chromatography on SiO2 EtOAc/Hex afforded the desired compound as a colorless foam (151 mg, 81%). MS (ESI) mass calcd. C18H13ClF3N5O, 407.08. m/z found 408.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.10-8.95 (m, 1H), 7.83-7.77 (m, 1H), 7.76-7.69 (m, 1H), 7.58-7.45 (m, 2H), 7.05-6.89 (m, 1H), 5.18-4.98 (m, 1H), 4.60-4.41 (m, 1H), 4.25-4.04 (m, 1H), 3.64-3.51 (m, 1H), 3.43-3.09 (m, 2H).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionThe material was dissolved in DCM
  3. filtrationFiltration
  4. customremoved the inorganic solids
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-13f44760f0744bf48e4ee11a5c01f6c9
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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