Cyclopentanone → HCID 21942654, compound

HRID 431973Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([NH2:21])[CH:14]=3)[O:10][N:9]=2)=[N:6][CH:7]=1.[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1.C([BH3-])#N.[Na+]>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([NH:21][CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:16]=[C:17]([C:19]#[N:20])[CH:18]=3)[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-(5-fluoropyrid-2-yl)-5-(3-amino-5-cyanophenyl) -1,2,4-oxadiazole (30 mg, 0.11 mmol), cyclopentanone (24 μL, 0.26 mmol), sodium cyanoborohydride, 1.0 M solution in tetrahydrofuran, (128 AL, 0.12 mmol) in acetic acid (4 mL) was heated at 60° C. for 1 hour. After cooling, the reaction mixture was diluted with ethyl acetate and then washed with water (2X) and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel chromatography using 20% ethyl acetate/hexanes afforded 15 mg (39%) of 3-(5-fluoropyrid-2-yl)-5-(3-cyano-5-cyclopentylaminophenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), δ (ppm): 8.69 (d, 1H), 8.25 (m, 1H), 7.79 (s, 1H), 7.61 (m, 2H), 6.99 (s, 1H), 4.17 (d, 1H), 3.88 (m, 1H), 2.10 (m, 1H), 1.74 (s, 2H), 1.50 (m, 1H), 1.27 (m, 2H), 0.87 (m, 2H).

Workup

temperatureAfter cooling
washwashed with water (2X) and saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-664c5054c83b4f0192f1bc5b08ded31e
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660753B2

Reaction notes

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