Acetic Acid → HCID 22288621, compound

HRID 968275Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[O:14][C:13]([CH2:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:18])=[N:12][N:11]=1.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O>[CH2:26]([N:23]1[CH2:24][CH2:25][CH:20]([NH:19][C:17](=[O:18])[CH2:16][CH2:15][C:13]2[O:14][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[N:11][N:12]=2)[CH2:21][CH2:22]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3-{5-[(2,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}-N-piperidin-4-ylpropanamide (200 mg) in N-methylpyrrolidinone (4 ml) was added benzaldehyde (115 μl) and glacial acetic acid (0.04 ml). The reaction mixture was then heated at 80° C. for 1 hour before being left to cool and sodium triacetoxyborohydride (242 mg) added. The mixture was then stirred at room temperature for 8 hours before being evaporated to dryness and the residue separated into basic and non-basic components using SCX chromatography. Basic fractions were combined and evaporated to dryness. The residue was purified by RPHPLC (MeCN with NH3 buffer). Fractions containing the desired product were combined and evaporated to dryness to give the title compound. (92 mg).

Workup

waitbefore being left
temperatureto cool
custombefore being evaporated to dryness
customthe residue separated into basic and non-basic components
customevaporated to dryness
customThe residue was purified by RPHPLC (MeCN with NH3 buffer)
additionFractions containing the desired product
customevaporated to dryness

Sources & evidence

ORD record: ord-00fdf851cb57443a9e6e75f250cff85c
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958350B2

Reaction notes

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