Cyclopropanecarboxylic acid → HCID 45889074, compound

HRID 929515Notes

Reaction equation

C1(C(O)=O)CC1.[C:7]([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:11])[CH:8]([CH3:10])[CH3:9]>>[CH:8]1([C:7]([N:12]2[CH2:13][CH2:14][CH:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=3)=[O:20])[CH2:16][CH2:17]2)=[O:11])[CH2:10][CH2:9]1

Participants

Reactant 2

HCID 15655Cyclopropanecarboxylic acid

HCID 24898133HCID 24898133, compound

Product 1

HCID 45889074HCID 45889074, compoundYield 89%

Procedure

Cyclopropanecarboxylic acid (36 mg, 0.418 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 (110 mg, 0.310 mmol, 89% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.80 (s, 1H), 7.57 (s, 4H), 6.37 (d, J=7.2 Hz, 1H), 4.16 (br, 2H), 3.74 (m, 1H), 3.25 (t, J=11.7 Hz, 1H), 2.81 (t, J=10.8 Hz, 1H), 1.98 (m, 1H), 1.85 (m, 2H), 1.30 (m, 2H), 0.7 (s, 4H).

Sources & evidence

ORD record: ord-078834cd4f3049b9b9e88f3317ce8a76
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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