3-(Trifluoromethyl)benzoyl chloride → HCID 54674307, compound

HRID 2363600Notes

Reaction equation

HRID 2363600 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.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36].FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1>>[CH3:21][CH:20]([CH3:22])[CH2:19][C@H:18]([N:23]1[CH2:28][CH2:27][CH2:25][CH2:24]1)[C:17]([NH:16][C@H:13]1[C@H:11]2[C@H:10]([CH2:9][N:8]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[C:32]([C:31]([F:42])([F:41])[F:30])[CH:33]=3)[CH2:12]2)[CH2:15][CH2:14]1)=[O:29]

Participants

4

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 54674009HCID 54674009, compound

Product 1

HCID 54674307HCID 54674307, 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 3-(trifluoromethyl)benzoyl chloride for 3-(trifluoromethyl)benzene-1-sulfonyl chloride in the procedures described in Example 319: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.41-8.17 (m, 1H), 8.14-8.05 (m, 1H), 8.01-7.78 (m, 1H), 7.76-7.66 (m, 1H), 7.53 (t, J=7.6, 1H), 4.51-4.29 (m, 1H), 4.20-4.00 (m, 1H), 3.89 (ddd, J=12.0, 6.6, 1.5, 1H), 3.74 (tdd, J=8.3, 5.2, 2.8, 1H), 3.67-3.45 (m, 1H), 3.32-3.13 (m, 2H), 2.87-2.57 (m, 6H), 2.23-2.02 (m, 1H), 1.96-1.78 (m, 2H), 1.73-1.55 (m, 6H), 1.47-1.24 (m, 1H), 1.04-0.79 (m, 6H); MS (ESI+) m/z 466 (M+H)+.

Sources & evidence

ORD record
ord-79bf5abf5a7946f9a73119709ff0529b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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