Tetrafluoroboric acid → Syn 1193

HRID 1742958Notes

Reaction equation

HRID 1742958 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:19][CH3:20])[C:11](F)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:21]2[CH2:23][CH2:22]2)[CH:7]=1)=[O:5])C.F[B-](F)(F)F.[H+].[N:30]1([CH:35]2[CH2:39][CH2:38][NH:37][CH2:36]2)[CH:34]=[CH:33][N:32]=[N:31]1>>[CH:21]1([N:8]2[C:9]3[C:14](=[CH:13][C:12]([F:17])=[C:11]([N:37]4[CH2:38][CH2:39][CH:35]([N:30]5[CH:34]=[CH:33][N:32]=[N:31]5)[CH2:36]4)[C:10]=3[O:19][CH3:20])[C:15](=[O:16])[C:6]([C:4]([OH:3])=[O:5])=[CH:7]2)[CH2:22][CH2:23]1

Participants

4

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 10758239Moxifloxacin difluoro methoxy ethyl esterHCID 152288371-(Pyrrolidin-3-YL)-1H-1,2,3-triazole

Product 1

HCID 476055Syn 1193

Procedure

Ethyl-6,7-difluoro-1-cyclopropyl-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate was complexed with fluoroboric acid according to the procedure described in Example 34, and then reacted with 3-(1,2,3-triazol-1-yl)pyrrolidine under the same reaction conditions, followed by hydrolysis to yield the desired product, m.p. 200°-201° C. 1H NMR (TFA) δ: 9.34 (s, 1H), 8.69 (d, 1H), 8.58 (d, 1H), 8.09 (d, 13.3HZ, 1H), 5.93-5.8 (m, 1H), 4.83-4.34 (m, 4H), 4.2-4.0 (m, 2H), 3.79 (s, 3H), 3.05-2.75 (m, 2H), 1.7-1.1 (m, 4H). Anal. calcd. for C20H20FN5O4 . 1/2 H2O: C, 56.87; H, 5.01; N, 16.58. Found: C, 56.86; H, 4.68; N, 16.24.

Workup

  1. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-19063efbe9a742a09bcad85261b2d597
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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