3,3,3-Trifluoropropionic acid → HCID 56971637, compound

HRID 929516Notes

Reaction equation

HRID 929516 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].C([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[O:22])[CH2:16][CH2:15]1)(=O)C(C)C>>[F:1][C:2]([F:8])([F:7])[CH2:3][C:4]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)=[O:22])[CH2:16][CH2:15]1)=[O:5]

Participants

3

Reactant 2

HCID 27779723,3,3-Trifluoropropionic acidHCID 24898133HCID 24898133, compound

Product 1

HCID 56971637HCID 56971637, compoundYield 87%

Procedure

3,3,3-Trifluoropropionic acid (67 mg, 0.522 mmol) was reacted with PTU (100 mg, 0.348 mmol) as the same manner as the synthesis of 1-(1-isobutyrylpiperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (120 mg, 0.302 mmol, 87% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.80 (s, 1H), 7.58 (s, 4H), 6.38 (d, J=7.8 Hz, 1H), 4.19 (d, J=13.3 Hz, 1H), 3.79 (d, J=13.8 Hz, 1H), 3.71 (m, 4H), 3.16 (t, J=11.1 Hz, 1H), 2.85 (t, J=11.7 Hz, 1H), 1.84 (m, 2H), 1.30 (m, 2H).

Sources & evidence

ORD record
ord-2be9d50f3e5a4f23bd45cad0ba62f0c7
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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