Triethylamine → HCID 54674156, compound

HRID 1092622Notes

Reaction equation

HRID 1092622 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][C@H:4]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:5]([NH:7][C@H:8]1[C@H:15]2[C@H:11]([CH2:12][NH:13][CH2:14]2)[CH2:10][CH2:9]1)=[O:6].C(N(CC)CC)C.[F:30][C:31]([F:43])([F:42])[C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1>ClCCl>[CH3:1][CH:2]([CH3:22])[CH2:3][C@H:4]([N:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:5]([NH:7][C@H:8]1[C@H:15]2[C@H:11]([CH2:12][N:13]([S:38]([C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:30])([F:42])[F:43])[CH:33]=3)(=[O:40])=[O:39])[CH2:14]2)[CH2:10][CH2:9]1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66591198HCID 66591198, compound

Product 1

HCID 54674156HCID 54674156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-methyl-2-morpholino-N-((3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)pentanamide (191 mg, 0.617 mmol), triethylamine (0.129 mL, 0.926 mmol), and 3-(trifluoromethyl)benzene-1-sulfonyl chloride (0.109 mL, 0.679 mmol) were combined in dichloromethane (0.5 mL). The reaction was stirred at room temperature for 3 hours. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.44 (d, J=6.2, 1H), 8.38 (s, 1H), 8.19 (d, J=7.9, 1H), 7.92 (d, J=7.8, 1H), 7.72 (t, J=7.9, 1H), 4.27-4.20 (m, 1H), 3.90 (dd, J=2.3, 10.0, 1H), 3.76-3.67 (m, 4H), 3.20 (ddd, J=3.9, 9.4, 10.9, 3H), 2.97 (dd, J=7.1, 9.6, 1H), 2.78-2.72 (m, 2H), 2.72-2.67 (m, 2H), 2.62-2.53 (m, 2H), 1.94 (dt, J=6.2, 12.1, 1H), 1.89-1.77 (m, 3H), 1.64-1.54 (m, 2H), 1.30 (ddt, J=6.5, 9.3, 12.8, 1H), 0.92 (d, J=4.4, 3H), 0.91 (d, J=4.4, 3H); MS (ESI+) m/z 518 (M+H)+.

Workup

  1. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e390387aac144f7ad87f86841fddac1
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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