Methylamine → 355805-96-8

HRID 1760155Notes

Reaction equation

[CH3:1][NH2:2].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:26])[CH2:19][C@@H:20]([OH:25])[CH2:21][C:22]([OH:24])=[O:23])=[C:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])[N:11]=2)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:26])[CH2:19][C@@H:20]([OH:25])[CH2:21][C:22]([O-:24])=[O:23])=[C:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])[N:11]=2)=[CH:6][CH:5]=1.[CH3:1][NH3+:2]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of methylamine in methanol (1.4 ml of a 40% solution) was added with stirring to a solution of (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoic acid (obtained as described below) at −5° C. The mixture was stirred at 30° C. for 90 minutes and then cooled to 3° C. The crystalline product was collected by filtration, washed with acetonitrile and dried under vacuum at 40° C. to give methylammonium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (3.85 g; 87.9% yield) as white crystals. (The same crystalline salt was obtained when a 40% solution of methylamine in water (1.1 ml) was used). The X-ray powder diffraction spectra (XRD) for a typical sample of the crystalline methylammonium salt is shown in FIG. 2 hereinafter. The ten most prominent peaks in the XRD occur at about 2-theta=8.2, 12.3, 15.7, 16.5, 17.6, 18.7,19.9, 21.0, 24.3 and 25.9°.

Workup

temperaturecooled to 3° C
filtrationThe crystalline product was collected by filtration
washwashed with acetonitrile
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-48d03e4a9535410f99f33868d83e45a0
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841554B2

Reaction notes

Loading…