Cyclopropanecarboxylic acid → HCID 45888834, compound

HRID 929509Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.[CH:22]1([C:25](O)=[O:26])[CH2:24][CH2:23]1>>[CH:22]1([C:25]([N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=3)=[O:9])[CH2:3][CH2:2]2)=[O:26])[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 15655Cyclopropanecarboxylic acid

HCID 49780164HCID 49780164, compound

Product 1

HCID 45888834HCID 45888834, compound

Procedure

Intermediate 42 (76 mg, 0.25 mmol) was reacted with cyclopropane carboxylic acid by Method E. Flash chromatography eluted with EtOAc and recrystallization from EtOAc:hexane afforded compound 52 (47 mg, 51%) as a white solid: Mp 195-196° C. 1H NMR (500 MHz, DMSO-d6) δ 8.56 (s, 1H), 7.47 (d, J=9.0 Hz, 2H), 7.22 (d, J=8.7 Hz, 2H), 6.25 (d, J=7.7 Hz, 1H), 4.15 (t, J=14.8 Hz, 2H), 3.77-3.68 (m, 1H), 3.25 (t, J=11.5 Hz, 1H, obscured), 2.81 (t, J=11.1 Hz, 1H), 1.98 (m, 1H), 1.93-1.75 (m, 2H), 1.41-1.17 (m, 2H), 0.75-0.65 (m, 4H). Purity 100%. HRMS calculated for C17H20F3N3O3+H+ 372.1535. found (ESI(+), [M+H]) 372.1546.

Workup

washFlash chromatography eluted with EtOAc and recrystallization from EtOAc

Sources & evidence

ORD record: ord-4a6df7aba6dc456f84aa73705a942108
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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