Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate → HCID 488922, compound

HRID 1450085Notes

Reaction equation

HRID 1450085 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:19])=[C:11]([Cl:18])[C:12]([F:17])=[CH:13]2)=[C:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])C.[NH2:23][C@H:24]([C@@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)[CH2:25][CH2:26][CH3:27]>C(#N)C>[ClH:18].[NH2:23][C@H:24]([C@@H:28]1[CH2:32][CH2:31][N:30]([C:11]2[C:12]([F:17])=[CH:13][N:14]3[C:9]([C:10]=2[CH3:19])=[C:8]([CH:20]2[CH2:21][CH2:22]2)[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]3=[O:16])[CH2:29]1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylateHCID 57150816HCID 57150816, compound

Product 1

HCID 488922HCID 488922, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 171 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 4 mL of anhydrous acetonitrile, reacted with (3R,1S)-3-(1-amino-3-methylpropyl)pyrrolidine (400 mg, 1.32 mmol, prepared as described by Plummer et al., Tetr. Lett. 34:7529-32 (1993), and carried forward as described in Example 253j-l, omitting the deprotection reaction, to give the title product. MS (high resolution) found: 402.2174; calc: 402.2193 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.60 (m, 2H), 0.95 (d, 3H), 1.06 (d, 3H), 1.75 (m, 1H), 2.13 (m, 1H), 229 (m, 2H), 2.50 (s, 3H), 3.66 (m, 3H), 3.78 (m, 1H), 3.97 (m, 1H), 7.88 (s, 1H), 908 (d, 1H), 13.82 (bs, 1H). Anal. Calcd for C22H29N3O3FCl.0.75 H2O: C, 58.53; H, 6.81; N, 9.31; Found: C, 58.88; H, 6.70; N, 9.26.

Workup

  1. customprepared
  2. customthe deprotection reaction

Sources & evidence

ORD record
ord-da6020cf563b46e4b1fb62f69d46be65
Source dataset
uspto-grants-1997_02
Patent number
US05599816

Reaction notes

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