Water → HCID 66590794, compound

HRID 2363594Notes

Reaction equation

HRID 2363594 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C@@H:14]1[C@@H:21]2[C@@H:17]([CH2:18][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:20]2)[CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-:3])=[O:2].S(OC)(O[CH3:39])(=O)=O.N12CCCN=C1CCCCC2.O>CN(C)C=O>[CH3:39][N:13]([C@@H:14]1[C@@H:21]2[C@@H:17]([CH2:18][N:19]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:20]2)[CH2:16][CH2:15]1)[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54674154HCID 54674154, compound

Product 1

HCID 66590794HCID 66590794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Nitro-N-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-yl)benzenesulfonamide (250 mg, 0.481 mmol) from Example 299 and dimethyl sulfate (0.138 mL, 1.444 mmol) were combined in N,N-dimethylformamide (3 mL) at 0° C. and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.145 mL, 0.962 mmol) was added dropwise. The reaction mixture was stirred for 0.5 hours, water was added, and the precipitate was collected by filtration. The resultant crude material was purified using a 12 g silica gel cartridge eluting with a gradient of 0-60% ethyl acetate/hexane over 20 minutes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.15 (dd, J=12.1, 4.7, 3H), 7.94 (d, J=8.3, 2H), 7.88 (dd, J=7.7, 1.3, 1H), 7.68 (dtd, J=19.1, 7.5, 1.3, 2H), 4.29 (dt, J=10.8, 7.0, 1H), 3.63 (dd, J=9.9, 1.5, 1H), 3.21 (dd, J=9.7, 2.3, 1H), 2.90 (s, 3H), 2.89-2.81 (m, 2H), 2.58-2.39 (m, 2H), 1.83-1.72 (m, 1H), 1.68-1.58 (m, 1H), 1.50 (qd, J=11.8, 7.3, 1H), 1.21 (ddd, J=19.4, 12.4, 7.1, 1H); MS (ESI+) m/z 551 (M+NH4)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customThe resultant crude material was purified
  3. washeluting with a gradient of 0-60% ethyl acetate/hexane over 20 minutes

Sources & evidence

ORD record
ord-2b6fccd4c1134b0682fb53bf1ecfab8e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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