Tetrahydrofuran → HCID 44578844, compound

HRID 1272712Notes

Reaction equation

[N:1]1([C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:30])=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20](C(NCCC)=O)[CH:19]=3)[CH:17]=2)=[O:11])[C:5]2[CH:6]=[CH:7]C=CC=2N=N1.[CH:31]1([CH2:34][NH2:35])[CH2:33][CH2:32]1.C1C[O:39][CH2:38]C1>>[CH:31]1([CH2:34][NH:35][C:38]([C:21]2[CH:20]=[CH:19][C:18]([C:16]3[C:15]([CH3:30])=[CH:14][CH:13]=[C:12]([C:10]([NH:1][CH2:5][CH2:6][CH3:7])=[O:11])[CH:17]=3)=[CH:23][CH:22]=2)=[O:39])[CH2:33][CH2:32]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 75646Cyclopropanemethanamine

HCID 18457814HCID 18457814, compound

Product 1

HCID 44578844HCID 44578844, compound

Procedure

5′-[(1H-1,2,3-Benzotriazol-1-yl)carbonyl]-2′-methyl-N-propyl-1,1′-biphenyl-3-carboxamide (25 mg, 0.062 mmol) in THF (1 ml) was mixed with cyclopropylmethylamine (7.2 μl) in THF (0.6 ml) and the reaction stirred at room temperature for 4 h. The reaction was loaded onto an SPE (aminopropyl, 1 g) and eluted with chloroform, ethyl acetate and methanol. The solvent was evaporated from the product fractions to give N4′-cyclopropylmethyl-6-methyl-N3-propyl-1,1′-biphenyl-3,4′-dicarboxamide. NMR: δH CDCl3 7.84, (2H, d), 7.68, (1H, dd), 7.62, (1H, d), 7.38, (2H, d), 7.33, (1H, d), 6.37, (1H, t), 6.26, (1H, t), 3.42, (2H, m), 3.35, (2H, m), 2.28, (3H, s), 1.64, (2H, m), 1.09, (1H, m), 0.98, (3H, t), 0.58, (2H, m), 0.30, (2H, m). LCMS: retention time 3.13 min, MH+351.

Workup

washeluted with chloroform, ethyl acetate and methanol
customThe solvent was evaporated from the product fractions

Sources & evidence

ORD record: ord-761c1c785d6d4f5dacbd90e5dd92c606
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208629B2

Reaction notes

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