Ethyl-pyrrolidin-3-ylmethyl-amine → HCID 13772805, compound

HRID 868082Notes

Reaction equation

HRID 868082 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH:7]=[C:6]([C:19]([OH:21])=[O:20])[C:5]2=[O:22].[CH2:23]([NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)[CH3:24]>C(#N)C>[CH2:23]([NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][N:29]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:22])[C:6]([C:19]([OH:21])=[O:20])=[CH:7][N:8]3[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:3][C:2]=2[F:1])[CH2:28]1)[CH3:24]

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 13772831HCID 13772831, compound

Product 1

HCID 13772805HCID 13772805, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 0.76 g (2.33 mmol) of 6,7,8-trifluoro-1-(2,2,2-trifluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 7.0 ml of acetonitrile was added 0.355 g (2.33 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene in 5 ml of acetonitrile followed by 0.29 g (2.33 mmol) of 3-[(ethylamino)methyl]pyrrolidine. The mixture was refluxed for one hour and kept at room temperature overnight. The solids were collected and washed with ether to give 0.77 g of 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, mp 222°-224° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. customThe solids were collected
  3. washwashed with ether

Sources & evidence

ORD record
ord-b6d9d0ef9ee7412298e0adf522c34846
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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