5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 70284622, compound

HRID 1742945Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.[OH:23][C@H:24]1[C@H:28]([N:29]2[CH:33]=[CH:32][N:31]=[N:30]2)[CH2:27][NH:26][CH2:25]1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][C@@H:28]([N:29]3[CH:33]=[CH:32][N:31]=[N:30]3)[C@H:24]([OH:23])[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (63 mg, 0.21 mmol), trans-3-hydroxy-4-(1,2,3-triazol-1-yl)-pyrrolidine hydrochloride (100 mg, 0.52 mmol) and diazabicycloundecane (79 mg, 0.52 mmol) in pyridine was heated at 110° C. for 20 h. The reaction mixture was concentrated and the residue was triturated with water. The separated solid was filtered, washed with water and acetonitrile and dried under vacuum at 40° C. Yield: 35 mg (40%), m.p. 261°-165.5° C. 1H NMR (TFA) δ: 1.33-1.51 (m, 4H), 4.24 (m, 2H), 4.60 (m, 2H), 4.92 (m, 1H), 5.20 (m, 1H), 5.79 (m, 1H), 8.59 (d, 1H), 8.78 (s, 1H), 9.15 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was triturated with water
filtrationThe separated solid was filtered
washwashed with water and acetonitrile
customdried under vacuum at 40° C

Sources & evidence

ORD record: ord-b8e5cb0ba92f43c68eea3b79c60f054c
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

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