Methanol → HCID 58168696, compound

HRID 38803Notes

Reaction equation

[O:1]=[S:2]1(=[O:35])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[C:11]([C:31]([F:34])([F:33])[F:32])=[N:12][C:13]([NH:16][C:17]34[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:25][C:19]([C:27]([O:29]C)=[O:28])([CH2:20]5)[CH2:18]3)[CH2:24]4)=[N:14][CH:15]=2)=[O:9])[CH2:4][CH2:3]1.CO.[OH-].[Na+]>O1CCCC1>[O:35]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]([C:10]2[C:11]([C:31]([F:34])([F:33])[F:32])=[N:12][C:13]([NH:16][C:17]34[CH2:24][CH:23]5[CH2:22][CH:21]([CH2:20][C:19]([C:27]([OH:29])=[O:28])([CH2:25]5)[CH2:18]3)[CH2:26]4)=[N:14][CH:15]=2)=[O:9])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of methyl 3-({5-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-4-(trifluoromethyl)pyrimidin-2-yl}amino)adamantane-1-carboxylate (500 mg) and methanol (2 mL), and tetrahydrofuran (2 mL) was added a 1 M aqueous sodium hydroxide solution (1.9 mL) at room temperature, followed by stirring at 60° C. for 3 hours. The solvent was evaporated under reduced pressure, and to the obtained residue were added water and 1 M hydrochloric acid, followed by stirring at room temperature for 30 minutes. The obtained precipitate was filtered and washed with water to obtain 3-({5-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-4-(trifluoromethyl)pyrimidin-2-yl}amino)adamantane-1-carboxylic acid (446 mg) as a white powder.

Workup

customThe solvent was evaporated under reduced pressure
additionto the obtained residue were added water and 1 M hydrochloric acid
stirringby stirring at room temperature for 30 minutes
filtrationThe obtained precipitate was filtered
washwashed with water

Sources & evidence

ORD record: ord-31e1f711486a4cc6b49935a0c47846dc
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524727B2

Reaction notes

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