3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 66590774, compound

HRID 2363602Notes

Reaction equation

C([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH:16][C:17](=[O:29])[C@@H:18]([N:23]3[CH2:28][CH2:27]O[CH2:25][CH2:24]3)[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1.[CH:30]1([S:33](Cl)(=[O:35])=[O:34])[CH2:32][CH2:31]1.FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1>>[CH:30]1([S:33]([N:8]2[CH2:12][C@H:11]3[C@H:13]([NH:16][C:17](=[O:29])[C@@H:18]([N:23]4[CH2:24][CH2:25][CH2:27][CH2:28]4)[CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:14][CH2:15][C@H:10]3[CH2:9]2)(=[O:35])=[O:34])[CH2:32][CH2:31]1

Participants

Reactant 3

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

HCID 2760919Cyclopropanesulfonyl chloride

HCID 54674009HCID 54674009, compound

Product 1

HCID 66590774HCID 66590774, compound

Procedure

The title compound was prepared by substituting (2S)-N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide from Example 250 for (S)-N-((3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-4-methyl-2-morpholinopentanamide and cyclopropanesulfonyl chloride for 3-(trifluoromethyl)benzene-1-sulfonyl chloride in the procedures described in Example 319: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.14 (d, J=7.3 Hz, 1H), 4.33-4.40 (m, 1H), 3.82 (dd, J=9.9, 2.6 Hz, 1H), 3.57 (dd, J=9.9, 7.0 Hz, 1H), 3.41 (dd, J=9.6, 7.0 Hz, 1H), 3.22 (dd, J=9.6, 3.2 Hz, 1H), 3.16 (dd, J=9.2, 5.1 Hz, 1H), 2.60-2.70 (m, 7H), 2.04 (dq, J=11.9, 5.9 Hz, 1H), 1.79-1.97 (m, 3H), 1.56-1.67 (m, 6H), 1.33-1.40 (m, 1H), 1.16-1.23 (m, 2H), 0.99 (d, J=6.3 Hz, 3H), 0.92 (d, J=6.4 Hz, 3H), 0.86-0.92 (m, 2H); MS (ESI+) m/z 398 (M+H)+.

Sources & evidence

ORD record: ord-31e249607aac4e3ab060509da51586f5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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