2-Methylbutanoic Acid → HCID 56971639, compound

HRID 929518Notes

Reaction equation

[CH3:1][CH:2]([CH2:6][CH3:7])[C:3](O)=[O:4].C([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[O:21])[CH2:15][CH2:14]1)(=O)C(C)C>>[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=2)=[O:21])[CH2:15][CH2:14]1)=[O:4]

Participants

Reactant 2

HCID 83142-Methylbutanoic Acid

HCID 24898133HCID 24898133, compound

Product 1

HCID 56971639HCID 56971639, compoundYield 88%

Procedure

2-Methylbutyric acid (50 mg, 0.487 mmol) was reacted with PTU (70 mg, 0.244 mmol) as the same manner as the synthesis of 1-(1-isobutyrylpiperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (80 mg, 0.215 mmol, 88% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.77 (d, J=8.4 Hz, 1H), 7.57 (s, 4H), 6.37 (s, 1H), 4.22 (m, 1H), 3.88 (d, J=13.2 Hz, 1H), 3.71 (m, 1H), 3.17 (t, J=12.8 Hz, 1H), 2.84 (m, 2H), 1.85 (m, 2H), 1.54 (m, 1H), 1.29 (m, 3H), 0.97 (s, 3H), 0.81 (d, J=6 Hz, 3H).

Sources & evidence

ORD record: ord-b06bf10c54bf4769a9bc794e69b280b1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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