Diisopropylethylamine → 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-1,2,4-oxadiazol-5-ylmethyl)-nicotinamide

HRID 469782Notes

Reaction equation

[CH:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([OH:13])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:54][C:55]([F:64])([F:63])[C:56]1[N:60]=[C:59]([CH2:61][NH2:62])[O:58][N:57]=1>CN(C=O)C>[CH:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([NH:62][CH2:61][C:59]2[O:58][N:57]=[C:56]([C:55]([F:64])([F:63])[F:54])[N:60]=2)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (Example 9c) (124 mg, 0.43 mmol) in DMF (4 mL) were added DIPEA (0.1 mL, 1.08 mmol) and HATU (204 mg, 0.54 mmol) at 25° C. The reaction mixture was stirred for 30 min at 25° C. To this was added C-(3-trifluoromethyl-1,2,4-oxadiazol-5-yl)-methylamine (CAN 944905-93-5) (60 mg, 0.36 mmol) and the reaction mixture was stirred for 12 h at 25° C. Volatiles were removed in vacuo and the resultant residue was purified by prep-HPLC to get 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-1,2,4-oxadiazol-5-ylmethyl)-nicotinamide (61 mg, 38.7%) as off-white solid; MS (ESI): 439 (M+H]+.

Workup

stirringthe reaction mixture was stirred for 12 h at 25° C
customVolatiles were removed in vacuo
customthe resultant residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-7051744875464644a3b792dddfc6fc2c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629166B2

Reaction notes

Loading…