Isopropylamine → HCID 21391890, compound

HRID 461689Notes

Reaction equation

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

Participants

Conditions

Temperature: -20 °C

Procedure

This example illustrates processes of the invention for preparing the compounds of formula C. In this example a mixture containing 12 g. (0.0314 mole) of 1,2-epoxy-3-(5-[2-(adamant-2-yl)ethylaminocarbonyl]thiazol-2-yloxy)propane, 12 g. (0.203 mole) of isopropylamine and 20 ml. of ethanol is allowed to stand at room temperature for 12 hours. The mixture is then evaporated under vacuum to remove the solvent and the resulting residue dissolved in 50 ml. of ethyl acetate and cooled to -20° C, and maintained at this temperature for 2 hours. The mixture is then filtered and the resulting filter cake washed with cold (about 0° C) ethyl ether and then recrystallized from ethyl acetate affording 1-isopropylamino-3-(5-[2-(adamant-2-yl)ethylaminocarbonyl]thiazol-2-yloxy)-propan-2-ol.

Workup

customfor preparing the compounds of formula C
customThe mixture is then evaporated under vacuum
customto remove the solvent
dissolutionthe resulting residue dissolved in 50 ml
temperaturemaintained at this temperature for 2 hours
filtrationThe mixture is then filtered
filtrationthe resulting filter cake
washwashed with cold (about 0° C) ethyl ether
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-631af8bf49954f2f8bc620956a80e367
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04064135

Reaction notes

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