2-Mercaptoethanol → HCID 66590418, compound

HRID 2363595Notes

Reaction equation

HRID 2363595 reaction equation
SCCO.[CH3:5][N:6]([C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][N:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:25]2)[CH2:21][CH2:20]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O.N12CCCN=C1CCCCC2.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:5][NH:6][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][N:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:25]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 66590794HCID 66590794, compound

Product 1

HCID 66590418HCID 66590418, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercaptoethanol (0.056 mL, 0.793 mmol) was added dropwise to a mixture of N-methyl-2-nitro-N-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-yl)benzenesulfonamide (235 mg, 0.440 mmol) from Example 300 and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.166 mL, 1.101 mmol) in N,N-dimethylformamide (1 mL) at room temperature. The reaction mixture was stirred for 30 minutes, and 1 N NaHCO3 solution was added, The mixture was extracted with dichloromethane, and the separated the organic layer was concentrated. The resultant crude material was purified using a SF15-12 g cartridge (Analogix®, Burlington, Wis.) with a gradient of 0-5.5% methanol (2 N NH3)/dichloromethane over 20 minutes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.17 (d, J=8.1, 2H), 7.94 (d, J=8.2, 2H), 4.93-4.86 (m, 1H), 3.34 (dd, J=9.8, 3.3, 1H), 3.14 (dd, J=9.7, 3.2, 1H), 3.06 (dd, J=9.7, 8.2, 1H), 2.65 (q, J=5.7, 1H), 2.57-2.46 (m, 1H), 2.29 (s, 3H), 2.25 (ddd, J=8.6, 5.0, 2.5, 1H), 1.86 (ddd, J=12.0, 8.6, 6.1, 1H), 1.80-1.72 (m, 1H), 1.61-1.32 (m, 1H), 1.32-1.19 (m, 2H); MS (ESI+) m/z 349 (M+H)+.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe separated the organic layer
  3. concentrationwas concentrated
  4. customThe resultant crude material was purified
  5. customover 20 minutes

Sources & evidence

ORD record
ord-9462375513c5417d98d109fae1b78c2b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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