Hydrochloric Acid → HCID 69428023, compound

HRID 1295505Notes

Reaction equation

HRID 1295505 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH:16]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=3)[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][S:27]([CH3:26])(=[O:29])=[O:28])[CH:20]=3)[CH:16]([CH2:15][CH2:14]2)[CH2:17]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 69430634HCID 69430634, compound

Product 1

HCID 69428023HCID 69428023, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

8-(3-Amino-phenyl)-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid benzyl ester (185 mg, 0.55 mmol) was dissolved in pyridine (3 mL), cooled to 0° C. then charged with methanesulfonylchloride (0.064 mL, 0.825 mmol) dropwise, causing a color change from yellow to bright orange. The reaction was warmed to room temperature and judged complete by APCI MS after 1 h. Following a 1N HCl quench (10 mL), the product was extracted with EtOAc (2×30 mL), washed with saturated aqueous NaHCO3 solution (1×30 mL), saturated aqueous NaCl solution (1×30 mL), dried over Na2SO4, filtered and concentrated to give an orange liquid (153 mg, 67%). (TLC 30% EtOAc/hexanes Rf 0.15); 1H NMR (400 MHz, CDCl3) δ 7.33–7.19 (m, 5H), 7.21 (t, J=7.9 Hz, 1H), 7.14 (s, 1H), 7.05 (d, J=7.9 Hz, 1H), 6.99 (d, J=7.9 Hz, 1H), 5.24 (s, 2H), 4.03 (d, J=12.5 Hz, 1H), 3.94 (d, J=12.6 Hz, 1H), 3.07 (d, J=12.5 Hz, 1H), 3.03 (d, J=12.5 Hz, 1H), 2.90 (s, 3H), 2.86 (s, 1H), 2.50 (br s, 1H), 2.44 (br s, 1H), 1.60 (m, 2H), 1.47 (m, 2H); APCI MS m/z 415.1 (M+1)+.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. customquench (10 mL)
  3. extractionthe product was extracted with EtOAc (2×30 mL)
  4. washwashed with saturated aqueous NaHCO3 solution (1×30 mL), saturated aqueous NaCl solution (1×30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee1eae0d279c4831ad02e47c56571930
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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