1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → HCID 69329556, compound

HRID 968483Notes

Reaction equation

HRID 968483 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][NH: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:37])=[C:33](F)[N:34]=3)[C:29](=[O:38])[C:28]([C:39]([OH:41])=[O:40])=[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][CH2:12][N:13]([C:33]4[N:34]=[C:35]5[C:30]([C:29](=[O:38])[C:28]([C:39]([OH:41])=[O:40])=[CH:27][N:26]5[CH:23]5[CH2:25][CH2:24]5)=[CH:31][C:32]=4[F:37])[CH2:14][CH2:15][C:9]=3[CH:8]=2)[CH2:5]1)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 151930221-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 69329130HCID 69329130, compound

Product 1

HCID 69329556HCID 69329556, 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[d]azepin-7-yl)-oxazolidin-5-ylmethyl]-acetamide (0.25 g) and 1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (0.23 g). The product was triturated with EtOH to purify. MS (APCI) AP+, 550. NMR (DMSO6)1.1 (m, 2H), 1.22 (m, 2H), 1.74 (s, 3H), 3.04 (m, 4H), 3.3 (m, 6H), 3.70 (m, 2H), 4.0 (m, 2H), 4.65 (m, 1H), 7.13 (d, 1H), 7.26 (dd, 1H), 7.35 (d, 1H), 8.0 (d, 1H), 8.14 (t, 1H), 8.52 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-238639d19bc744f8b2cc3f2d2675aa05
Source dataset
uspto-grants-2007_12
Patent number
US07304050B2

Reaction notes

Loading…