Triethylamine → N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide

HRID 1092553Notes

Reaction equation

HRID 1092553 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][CH:17]3[CH2:19][CH2:18]3)[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1.CN(C1C=CC=CN=1)C>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([N:16]([CH:17]3[CH2:18][CH2:19]3)[S:35]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:39])[F:40])[CH:30]=3)(=[O:37])=[O:36])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 46213241(3aS*,4S*,6aR*)-2-benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 68413617N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3aS*,4S*,6aR*)-2-Benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine (382 mg, 1.490 mmol) from Example 198, triethylamine (312 μL, 2.235 mmol), and 3-(trifluoromethyl)benzene-1-sulfonyl chloride (262 μL, 1.639 mmol) were combined in tetrahydrofuran (7 mL). A catalytic amount of (dimethylamino)pyridine was added, and the reaction mixture was stirred at room temperature overnight. The solvent was reduced in volume, and the crude material applied to silica gel and eluted with 20% to 100% ethyl acetate/hexanes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.46 (s, 1H), 8.31 (d, J=7.9, 1H), 7.93 (d, J=7.8, 1H), 7.74 (t, J=7.9, 1H), 7.41 (d, J=7.2, 2H), 7.36 (t, J=7.4, 2H), 7.29 (t, J=7.2, 1H), 3.97 (ddd, J=6.1, 7.7, 13.5, 1H), 3.54-3.45 (m, 2H), 3.17 (dt, J=5.9, 11.8, 1H), 2.82 (dd, J=3.6, 9.7, 1H), 2.55 (t, J=8.2, 1H), 2.51-2.43 (m, 2H), 2.36-2.22 (m, 2H), 1.88-1.82 (m, 1H), 1.57 (dt, J=5.9, 11.6, 1H), 1.43-1.32 (m, 3H), 1.05-0.98 (m, 1H), 0.80 (ddd, J=6.9, 9.8, 12.4, 1H), 0.73-0.65 (m, 1H); MS (ESI+) m/z 465 (M+H)+.

Workup

  1. washeluted with 20% to 100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0aa60b46c25f45aaa11d58d9590301a3
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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