Ethyl-pyrrolidin-3-ylmethyl-amine → HCID 461889, compound

HRID 868085Notes

Reaction equation

HRID 868085 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:17])=[C:12](F)[C:13]=3[F:15])[C:8](=[O:18])[C:7]([C:19]([OH:21])=[O:20])=[CH:6]2)[CH2:3][CH2:2]1.[CH2:22]([NH:24][CH2:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)[CH3:23]>C(#N)C>[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:17])=[C:12]([N:28]4[CH2:29][CH2:30][CH:26]([CH2:25][NH:24][CH2:22][CH3:23])[CH2:27]4)[C:13]=3[F:15])[C:8](=[O:18])[C:7]([C:19]([OH:21])=[O:20])=[CH:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 13772832HCID 13772832, compound

Product 1

HCID 461889HCID 461889, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 1.0 g (3.36 mmol) of 1-(cyclopropylmethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 8 ml of acetonitrile was added 0.51 g (3.36 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.43 g (3.36 mmol) of 3-[(ethylamino)methyl]pyrrolidine each in 1 ml of acetonitrile. The mixture was refluxed for two hours and stirred overnight at room temperature. The mixture was filtered, and washed with ether to give 0.935 g of 1-(cyclopropylmethyl)-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecrboxylic acid, mp 185°-188° C.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. filtrationThe mixture was filtered
  3. washwashed with ether
  4. customto give 0.935 g of 1-(cyclopropylmethyl)-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecrboxylic acid, mp 185°-188° C.

Sources & evidence

ORD record
ord-eabeda6e6637452ebb95296d955b98d1
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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