Diisopropylethylamine → 5-Methyl-oxazole-4-carboxylic acid [5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide

HRID 1253780Notes

Reaction equation

[CH3:1][C:2]1[O:6][CH:5]=[N:4][C:3]=1[C:7]([OH:9])=O.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.[CH:43]1([C:48]2[CH:49]=[C:50]([NH2:60])[CH:51]=[N:52][C:53]=2[O:54][CH2:55][C:56]([F:59])([F:58])[F:57])[CH2:47][CH2:46][CH2:45][CH2:44]1>CN(C=O)C>[CH:43]1([C:48]2[CH:49]=[C:50]([NH:60][C:7]([C:3]3[N:4]=[CH:5][O:6][C:2]=3[CH3:1])=[O:9])[CH:51]=[N:52][C:53]=2[O:54][CH2:55][C:56]([F:57])([F:58])[F:59])[CH2:44][CH2:45][CH2:46][CH2:47]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-methyl-4-oxazolecarboxylic acid (CAN 103879-58-9) (73 mg, 0.57 mmol) in DMF (4 mL) were added DIPEA (0.1 mL, 1.15 mmol) and HATU (219 mg, 0.57 mmol) at 25° C. The reaction mixture was stirred for 30 min at 25° C. Then, 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (Example 1c) (100 mg, 0.38 mmol) was added and the reaction mixture was stirred at 25° C. for 12 h. Volatiles were removed in vacuo and the resultant residue was purified by prep-HPLC to get the title compound (30 mg, 21.3%) as off-white solid. MS (ESI): 370 [M+H]+.

Workup

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

Sources & evidence

ORD record: ord-b3d72266df3148e6b8160523c197df41
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455501B2

Reaction notes

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