Morpholine → HCID 68983949, compound

HRID 1467892Notes

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[CH2:36][CH2:35][O: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[CH2:36][CH2:35][O: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

Reactant 2

HCID 8083Morpholine

HCID 68983635HCID 68983635, compound

Product 1

HCID 68983949HCID 68983949, compoundYield 40%

Procedure

N-Cyclopropyl-N-[1-(3-morpholin-4-yl-hexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (42) was prepared by reacting N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethylbenzene-sulfonamide (30) (250 mg, 0.56 mmol) and morpholine (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 42 (120 mg, 40%) as a white solid. LC: 100%. MS: m/z=532.3, 533.3 (M+H). 1H NMR (400 MHz, CDCl3): (1:1 mixture of rotamers) δ 8.15 (1H, s), 8.07 (1H, d, J=7.5 Hz), 7.88 (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), 3.96 (1H, d, J=15 Hz), 3.70 (4H, m), 3.09 (2H, m), 2.64-2.44 (6H, m), 2.20 (1H, dd, J=8.8 Hz), 1.99 (1H, m), 1.50-1.25 (4H, m), 1.02-0.70 (7H, m).

Workup

customN-Cyclopropyl-N-[1-(3-morpholin-4-yl-hexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (42) was prepared
customThe residue was chromatographed over flash silica eluting with ethyl acetate:methanol:ammonia (100:10:1)

Sources & evidence

ORD record: ord-b66d13e3012c430fbb6b8d72309027c4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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