Trifluoroacetic acid → 2-[3-(Pyrid-2-yl)isoxazol-5-yl]pyrrolidine-1-carboximidamide

HRID 2105231Notes

Reaction equation

C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[C:30]1[O:34][N:33]=[C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[CH:31]=1)=[N:17]C(OC(C)(C)C)=O)=O)(C)(C)C>C(Cl)Cl>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:32]1[CH:31]=[C:30]([CH:26]2[CH2:27][CH2:28][CH2:29][N:25]2[C:16](=[NH:15])[NH2:17])[O:34][N:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

TFA (30 ml) was added to a cooled solution of N,N′-di(tert-butyloxycarbonyl)-2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidine-1-carboximidamide (Method 39) in DCM (150 ml) at 0° C. The mixture was stirred 0° C. for one hour, allowed to warm to ambient temperature and stirred for a further 18 hours. The volatiles were removed by evaporation and the residue triturated from DCM/ether/hexane. The product was collected by filtration to give the title compound (2.2 g, >100%).

Workup

temperatureto warm to ambient temperature
stirringstirred for a further 18 hours
customThe volatiles were removed by evaporation
customthe residue triturated from DCM/ether/hexane
filtrationThe product was collected by filtration

Sources & evidence

ORD record: ord-8dc3eb1ef75b4f608fc2a39fd14c2e03
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579349B2

Reaction notes

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