(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride → HCID 86720708, compound

HRID 1497986Notes

Reaction equation

HRID 1497986 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.[C:22](Cl)(=[O:32])[O:23][C@@H:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1>CC#N.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([C:22]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:32])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 2

HCID 86676896(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochlorideHCID 86720706HCID 86720706, compound

Product 1

HCID 86720708HCID 86720708, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of methyl 3-fluoro-5-(((2-fluorophenyl)amino)methyl)benzoate (133 mg, 0.48 mmol) and (R)-quinuclidin-3-yl carbonochloridate hydrochloride (163 mg, 0.72 mmol) in anhydrous CH3CN (6 mL) was heated to 100° C. for 30 minutes under microwave irradiation. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL) and saturated aqueous NaHCO3 (20 mL). The layers were separated and the organic phase was dried over Na2SO4. The mixture was filtered and the solvent was removed in vacuo to yield the title compound which was used directly in the next step without any further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationThe mixture was filtered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c6b2b7fc782849a5b6516fadea8ed22e
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

Loading…