Methanol → HCID 117678548, compound

HRID 1474741Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][C@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][C:23]([CH2:26][O:27][CH3:28])=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH:5]=[C:4]([F:29])[C:3]=1[CH2:30][C:31](O)=[O:32].CO>O1CCCC1>[F:29][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][C@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[N:21]=[CH:22][C:23]([CH2:26][O:27][CH3:28])=[CH:24][N:25]=3)[CH2:18][CH2:19]2)[CH:7]=[C:2]([F:1])[C:3]=1[CH2:30][CH2:31][OH:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of {2,6-difluoro-4-[2-((1R,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethoxy]phenyl}acetic acid (72.0 mg, 0.125 mmol) in 1 ml anhydrous tetrahydrofuran at 0° C. was added 1 M borane-tetrahydrofuran complex (0.375 ml, 0.375 mmol) dropwise. The reaction mixture was stirred at 50° C. for an hour. The mixture was diluted by addition of 1 ml of methanol, concentrated under reduced pressure, and the residue purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 25-95% acetonitrile in 0.1% formic acid in water gradient) to afford the title compound. LC/MS (m/z): 448.4 (M+H)+. Human EC50: 7.2 nM

Workup

concentrationconcentrated under reduced pressure
customthe residue purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 25-95% acetonitrile in 0.1% formic acid in water gradient)

Sources & evidence

ORD record: ord-8cfaf445720d471c837b492f6c7c9af5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018224B2

Reaction notes

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