Hydrochloric Acid → HCID 178484140, compound

HRID 1159398Notes

Reaction equation

HRID 1159398 reaction equation
Cl.[F:2][C:3]1[C:23]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C@H:6]1[CH2:9][C@H:8]([CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)[CH2:7]1>O1CCOCC1>[F:2][C:3]1[C:23]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C@H:6]1[CH2:9][C@H:8]([CH2:10][NH:11][CH3:12])[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178484141HCID 178484141, compound

Product 1

HCID 178484140HCID 178484140, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl in dioxane (6.05 ml) was added to a solution of example 390, tert-butyl ({trans-3-[2-fluoro-3-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)methylcarbamate (1.9 g, 4.84 mmol) in 2 ml of dioxane. The mixture was stirred for 20 h and evaporated to dryness. The residue was recrystallized from MeOH-Et2O. The crystals were separated by filtration and dryed, then CH2Cl2 (30 mL) and saturated 10N NaOH (pH 12) were added under stirring. The layers were separated; the water solution was extracted with CH2Cl2 (3×20 mL). The combined extracts were dried (Na2SO4) and evaporated; the residue was dried in vacuo to give the title compound (1.1 g, 79%) as a yellow oil. LC/MS data: 294.4, 293.4 (M+H) (calculated for C17H25FN2O 292.5). 1H NMR-data (DMSO-d6): 6.98-7.04 (m, 1H, Ar—H); 6.88-6.94 (m, 1H, Ar); 6.78-6.84 (m, 1H, Ar—H); 4.77-4.86 (m, 1H), 3.60 (s, 2H); 2.57 (d, 2H, J=7.4 Hz); 2.33-2.47 (m, 5H); 2.30 (s, 3H, NCH3); 2.20-2.28 (m, 4H); 1.64-1.73 (m, 4H).

Workup

  1. customevaporated to dryness
  2. customThe residue was recrystallized from MeOH-Et2O
  3. customThe crystals were separated by filtration
  4. additionCH2Cl2 (30 mL) and saturated 10N NaOH (pH 12) were added
  5. stirringunder stirring
  6. customThe layers were separated
  7. extractionthe water solution was extracted with CH2Cl2 (3×20 mL)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customevaporated
  10. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-1db35eed8e5d4890a1857e122056d67d
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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