Butyric Acid → HCID 56971638, compound

HRID 929517Notes

Reaction equation

[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].C([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[O:20])[CH2:14][CH2:13]1)(=O)C(C)C>>[C:1]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)=[O:20])[CH2:14][CH2:13]1)(=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 264Butyric Acid

HCID 24898133HCID 24898133, compound

Product 1

HCID 56971638HCID 56971638, compoundYield 91%

Procedure

Butyric acid (37 mg, 0.418 mmol) was reacted with PTU (80 mg, 0.278 mmol) as the same manner as the synthesis of 1-(1-isobutyrylpiperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (91 mg, 0.255 mmol, 91% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.79 (s, 1H), 7.56 (s, 4H), 6.36 (d, J=7.8 Hz, 1H), 4.19 (d, J=12.9 Hz, 1H), 3.75 (d, J=14.4 Hz, 1H), 3.12 (t, J=11.4 Hz, 1H), 2.77 (m, J=12 Hz, 1H), 2.28 (t, J=7.5 Hz, 2H), 1.82 (t, J=13.2 Hz, 2H), 1.49 (m, 2H), 1.29 (m, 3H), 0.88 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record: ord-0886bc4ee1254fafb536bce3221e2e51
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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