Ethanol → HCID 59578056, compound

HRID 2194170Notes

Reaction equation

Cl[C:2]1[C:7]([S:8]([N:11]2[CH2:32][CH2:31][C:14]3([C:18](=[O:19])[N:17]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=4)[CH2:16][CH2:15]3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:33][NH2:34].C(O)C>C(OCC)(=O)C>[CH3:33][NH:34][C:2]1[C:7]([S:8]([N:11]2[CH2:32][CH2:31][C:14]3([C:18](=[O:19])[N:17]([C:20]4[CH:21]=[CH:22][C:23]([O:26][C:27]([F:29])([F:28])[F:30])=[CH:24][CH:25]=4)[CH2:16][CH2:15]3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8-(2-chloro-pyridine-3-sulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 188, 40 mg, 0.08 mmol) and 8M methyl amine solution in ethanol (408 uL, 3.26 mmol) and was heated to 90° C. in a sealed tube for 48 h. The reaction mixture was transferred to a round bottom flask and concentrated in vacuo to give a crude residue which was diluted with ethyl acetate and washed with water, sat. NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and evaporated under reduced pressure to give a crude residue which was purified by flash column chromatography using Amine-Silica to yield the desired product as a white solid (39 mg, 98%). MS (ESI): 485.2 (MH+).

Workup

customThe reaction mixture was transferred to a round bottom flask
concentrationconcentrated in vacuo
customto give a crude residue which
washwashed with water, sat. NaHCO3 and brine
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated under reduced pressure
customto give a crude residue which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-0045f97209444ada9105e84fc0b88692
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329904B2

Reaction notes

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