Diisopropylethylamine → HCID 70395651, compound

HRID 477022Notes

Reaction equation

HRID 477022 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[CH3:22][O:23][C:24]([NH:26][C@H:27]1[C@H:31]([CH2:32][CH3:33])[CH2:30][NH:29][CH2:28]1)=[O:25].C(N(C(C)C)CC)(C)C>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:29]2[CH2:30][C@@H:31]([CH2:32][CH3:33])[C@H:27]([NH:26][C:24]([O:23][CH3:22])=[O:25])[CH2:28]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 70396196HCID 70396196, compound

Product 1

HCID 70395651HCID 70395651, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.36 g), trans-3-methoxycarbonylamino-4-ethyl pyrrolidine (0.94 g), diisopropylethylamine (0.88 g), and acetonitrile (20 ml) was refluxed for 15 hours. The precipitated crystals wee collected by filtration, and dried to give 5-amino-1-cyclopropyl-7-(trans-3-methoxycarbonylamino-4-ethyl-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.15 g), recrystallized from chloroform-ethanol, m.p. 231°-232° C.

Workup

  1. temperaturewas refluxed for 15 hours
  2. filtrationThe precipitated crystals wee collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-6142b69b936b49ffaf42c5ea7536e7cb
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

Loading…