4-Methylmorpholine → HCID 178484855, compound

HRID 1063624Notes

Reaction equation

[CH3:1][N:2]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:5][CH2:4]1.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CN1CCOCC1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[OH:28][CH:29]1[CH2:34][CH2:33][N:32]([C:12](=[O:14])[CH2:11][CH2:10][O:9][C@H:6]2[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[S:15]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:22][CH:23]=3)(=[O:16])=[O:17])[CH2:4][CH2:5]2)[CH2:31][CH2:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

100 mg (0.24 mmol) of trans-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid in 3 mL of CH2Cl2 were treated with 21.3 mg (0.36 mmol, 1.5 eq) of 4-hydroxypiperidine and 0.40 mL (0.36 mmol, 1.5 eq) of NMM. The solution was cooled to 0° C. and 60.9 mg (0.31 mmol, 1.3 eq) of EDCI and 7.5 mg (0.05 mmol, 0.2 eq) of HOBT were added. The mixture was stirred at RT over night, and was then partitioned between CH2Cl2 and a saturated aqueous solution of Na2CO3. The organic phase was washed with a solution of KHSO4 and brine, dried over Na2SO4 and evaporated. Column chromatography with CH2Cl2:MeOH 98:2 gave 97.1 mg (81%) of trans-N-{4-[3-(4-hydroxy-piperidin-1-yl)-3-oxo-propoxy]-cyclohexyl}-N-methyl-4-trifluoromethyl-benzenesulfonamide as white powder, MS: 493 (MH+).

Workup

customwas then partitioned between CH2Cl2
washThe organic phase was washed with a solution of KHSO4 and brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-264c2a6e3a9a439b8c5e7c109608b8a6
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06965048B2

Reaction notes

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