Tetrahydrofuran → HCID 86222010, compound

HRID 1272706Notes

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([NH2:34])[CH2:33][CH2:32]1.C1C[O:38][CH2:37]C1>>[CH:31]1([NH:34][C:37]([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:38])[CH2:33][CH2:32]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 69828Cyclopropylamine

HCID 18457814HCID 18457814, compound

Product 1

HCID 86222010HCID 86222010, 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 cyclopropylamine (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′-cyclopropyl-6-methyl-N3-propyl-1,1′-biphenyl-3,4′-dicarboxamide. NMR: δH CDCl3 7.79, (2H, d), 7.67, (1H, dd), 7.60, (1H, d), 7.32, (3H, m), 6.56, (1H, s), 6.35, (1H, t), 3.41, (2H, q), 2.92, (1H, m), 2.25, (3H, s), 1.63, (2H, m), 0.97, (3H, t), 0.88, (2H, m), 0.65, (2H, m). LCMS: retention time 2.95 min, MH+337.

Workup

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

Sources & evidence

ORD record: ord-7d600b76f3a8422f946234b881824d35
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208629B2

Reaction notes

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