4-Methylmorpholine → HCID 178483788, compound

HRID 2118230Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

120 mg (0.29 mmol) of trans-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid in 3 mL of CH2Cl2 were treated with 0.057 mL (0.44 mmol, 1.5 eq) of N,N,N′-trimethylethylenediamine and 0.48 mL (0.36 mmol, 1.5 eq) of NMM. The solution was cooled to 0° C. and 73.0 mg (0.38 mmol, 1.3 eq) of EDCI and 9 mg (0.06 mmol, 0.2 eq) of HOBT were added. The mixture was stirred at RT for 2 days, partitioned between CH2Cl2 and a saturated aqueous solution of NaHCO3. The organic phase was washed with brine, dried over Na2SO4 and evaporated. Column chromatography with CH2Cl2:MeOH 9:1 gave 118 mg (82%) of trans-N-(2-dimethylamino-ethyl)-N-methyl-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionamide as colorless oil, MS: 494 (MH+).

Workup

custompartitioned between CH2Cl2
washThe organic phase was washed with brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-be91c7718f25456ab72d108557bdb504
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442791B2

Reaction notes

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