1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 69329552, compound

HRID 968482Notes

Reaction equation

HRID 968482 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)[CH2:5][CH:4]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:3]1.[CH:23]1([N:26]2[C:35]3[C:30](=[CH:31][C:32]([F:38])=[C:33](F)[C:34]=3[F:36])[C:29](=[O:39])[C:28]([C:40]([OH:42])=[O:41])=[CH:27]2)[CH2:25][CH2:24]1>>[C:20]([NH:19][CH2:18][CH:4]1[O:3][C:2](=[O:1])[N:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][N:12]([C:33]4[C:34]([F:36])=[C:35]5[C:30]([C:29](=[O:39])[C:28]([C:40]([OH:42])=[O:41])=[CH:27][N:26]5[CH:23]5[CH2:25][CH2:24]5)=[CH:31][C:32]=4[F:38])[CH2:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)[CH2:5]1)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 22269656HCID 22269656, compound

Product 1

HCID 69329552HCID 69329552, compound

Procedure

The title compound was prepared in a procedure analogous to that used in Example 6, using N-[2-Oxo-3-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl)-oxazolidin-5-ylmethyl]-acetamide (0.25 g) and 1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.23 g). The product was triturated with EtOH to purify. MS (APCI)AP+, 567. NMR (DMSO6)1.1-1.22 (m, 4H), 1.78 (s, 3H), 1.87 (brm, 2H), 3.0 (brs, 2H), 3.38 (t, 2H), 3.7 (m, 3H), 4.04 (t, 2H), 4.43 (s, 2H), 4.61 (m, 1H), 7.13 (d, 1H), 7.26 (d, 1H), 7.35 (s, 1H), 7.78 (d, 1H), 8.2 (t, 1H), 8.61 (s, 1H).

Workup

  1. customThe product was triturated with EtOH
  2. customto purify

Sources & evidence

ORD record
ord-30ee51e9ec3646f2b179e5233cb3cc48
Source dataset
uspto-grants-2007_12
Patent number
US07304050B2

Reaction notes

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