4,4,4-Trifluorobutanoic acid → HCID 56971640, compound

HRID 929519Notes

Reaction equation

HRID 929519 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:23])[CH2:17][CH2:16]1)(=O)C(C)C>>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=2)=[O:23])[CH2:17][CH2:16]1)=[O:6]

Participants

3

Reactant 2

HCID 27770854,4,4-Trifluorobutanoic acidHCID 24898133HCID 24898133, compound

Product 1

HCID 56971640HCID 56971640, compoundYield 70%

Procedure

4,4,4-Trifluorobutanoic acid (59 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 (80 mg, 0.194 mmol, 70% 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=13.8 Hz, 1H), 3.79 (d, J=13.8 Hz, 1H), 3.77 (m, 1H), 3.16 (t, J=12.3 Hz, 1H), 2.84 (m, J=11.4 Hz, 1H), 2.60 (d, J=6.3 Hz, 2H), 2.59 (m, 2H), 1.85 (br, 2H), 1.30 (m, 2H).

Sources & evidence

ORD record
ord-f25ca79bb7924bf0aff23ca3556fe392
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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