Piperazine → HCID 59526801, compound

HRID 1920705Notes

Reaction equation

HRID 1920705 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:25])=[C:17](F)[C:18]=3[O:20][CH:21]([F:23])[F:22])[C:13](=[O:26])[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11]2[S:32]([CH3:35])(=[O:34])=[O:33])[CH2:9][CH2:8]1.NC([C@@H]1CCN(C2C(OC)=C3C(C(=O)C(C(OCC)=O)=C(S(C)(=O)=O)N3C3CC3)=CC=2F)C1)(C)C>>[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:25])=[C:17]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)[C:18]=3[O:20][CH:21]([F:23])[F:22])[C:13](=[O:26])[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11]2[S:32]([CH3:35])(=[O:33])=[O:34])[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 58420505HCID 58420505, compoundHCID 59687293HCID 59687293, compound

Product 1

HCID 59526801HCID 59526801, compound

Procedure

The title compound is prepared from piperazine and ethyl 1-cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-2-(methylsulfonyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate using a procedure analogous to that describing the preparation of (R)-ethyl 7-(3-(2-aminopropan-2-yl)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-2-(methylsulfonyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate. (See US 2008071086, and Hashimoto, et al., 2007) 1H NMR (CDCl3): δ 0.30-0.33 (m, 1H), 0.84-0.88 (m, 1H), 0.99-1.04 (m, 1H), 1.20-1.25 (m, 1H), 1.38 (t, J=7.2 Hz, 3H), 2.95-3.21 (m, 6H), 3.44 (s, 3H), 3.51-3.58 (m, 2H), 4.13-4.18 (m, 1H), 4.36-4.48 (m, 2H), 6.54 (dd, J=76.0 Hz, 73.0 Hz, 1H), 7.72 (d, J=12.0 Hz, 1H). 19F NMR (CDCl3): δ −120.4 (s, 1F), −82.1 (s, 2F). LCMS: m/z calcd for C21H24F3N3O6S ([M]+) 503. found ([M+H]+) 504.

Sources & evidence

ORD record
ord-7c851e368ced41138724251d124f70a1
Source dataset
uspto-grants-2012_05
Patent number
US08173636B2

Reaction notes

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