Pyrrolidine → HCID 68983650, compound

HRID 1467893Notes

Reaction equation

HRID 1467893 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:30])[CH:25]=[CH:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:30])[CH2:25][CH:26]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 68983635HCID 68983635, compound

Product 1

HCID 68983650HCID 68983650, compoundYield 48%

Procedure

N-Cyclopropyl-N-[1-(3-pyrrolidin-1-ylhexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (43) was prepared by reacting N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethyl-benzenesulfonamide (30) (250 mg, 0.56 mmol) and pyrrolidine (2 mL) as described in Example 26 above. The residue was chromatographed over flash silica eluting with ethyl acetate:methanol:ammonia (100:10:1) to give the title compound 43 as a white solid (140 mg, 48%). LC: 98.9%. m/z=516.3, 517.3 (M+H). 1H NMR (400 MHz, CDCl3): (1:1 mixture of rotamers) δ 8.14 (1H, s), 8.05 (1H, d, J=7.5 Hz), 7.86 (1H, d, J=7.5 Hz), 7.70 (1H, t, J=7.5 Hz), 4.75 (1H, d, J=15 Hz), 4.10 (1H, m), 3.97 (1H, d, J=15 Hz), 3.05 (2H, m), 2.65-2.45 (6H, m), 2.35 (1H, m), 1.96 (1H, m), 1.85-1.30 (16H, m), 0.98 (1H, m), 0.92-0.70 (6H, m).

Workup

  1. customN-Cyclopropyl-N-[1-(3-pyrrolidin-1-ylhexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (43) was prepared
  2. customThe residue was chromatographed over flash silica eluting with ethyl acetate:methanol:ammonia (100:10:1)

Sources & evidence

ORD record
ord-d200daac9d2f4578af28103ff34ed557
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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