Triethylamine → HCID 54539870, compound

HRID 373701Notes

Reaction equation

HRID 373701 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][NH:10][CH2:11][C:12]12[CH2:17][CH:16]1[CH2:15][NH:14][CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:25]1([N:28]2[C:37]3[C:32](=[CH:33][C:34]([F:39])=[C:35](F)[CH:36]=3)[C:31](=[O:40])[C:30]([C:41]([OH:43])=[O:42])=[CH:29]2)[CH2:27][CH2:26]1>C(#N)C>[C:1]([O:5][C:6]([CH2:8][CH2:9][NH:10][CH2:11][C:12]12[CH2:17][CH:16]1[CH2:15][N:14]([C:35]1[CH:36]=[C:37]3[C:32]([C:31](=[O:40])[C:30]([C:41]([OH:43])=[O:42])=[CH:29][N:28]3[CH:25]3[CH2:27][CH2:26]3)=[CH:33][C:34]=1[F:39])[CH2:13]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 53914838HCID 53914838, compound

Product 1

HCID 54539870HCID 54539870, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[N-(tert-butoxycarbonyl)ethylamino-methyl]-3-azabicyclo[3.1.0]hexane (45.3 mg, 0.18 mmol) and triethylamine (50 μl, 0.36 mmol) in acetonitrile (5 ml) was treated with 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (50.0 mg, 0.18 mmol) and heated to 80° for 18 hours. Filtration of the reaction mixture provided the title product as a white solid (26.8 mg, 0.055 mmol, 31% yield). 1H NMR (CDCl3): 8.67 (s, 1H), 7.90 (d, J=15 Hz, 1H), 6.89 (d, J=7 Hz, 1H), 3.87 (bs, 2H), 3.5 (m, 5H), 3.3 (bs, 2H), 1.6 (m, 1H), 1.49 (s, 9H), 1.33 (m, 2H), 1.14 (m, 5H), 0.83 (m, 1H), 0.68 (m, 1 H).

Workup

  1. temperatureheated to 80° for 18 hours
  2. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-9582cf9963ff40abad57b9ef4f302944
Source dataset
uspto-grants-1992_11
Patent number
US05164402

Reaction notes

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