Diisopropylethylamine → Ethyl 7-((1s,4s)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo(2.2.1)hept-2-yl)-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696943Notes

Reaction equation

HRID 1696943 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1[F:29].[C@H:30]12[CH2:36][C@H:33]([NH:34][CH2:35]1)[CH2:32][N:31]2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[C:40]([O:39][C:37]([N:31]1[CH2:32][C@@H:33]2[CH2:36][C@H:30]1[CH2:35][N:34]2[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1[F:29])=[O:38])([CH3:43])([CH3:41])[CH3:42]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67274956Ethyl 7-((1s,4s)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo(2.2.1)hept-2-yl)-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 7F (500 mg), tert-butyl (1S,4S)-(−)-2,5-diazabicyclo(2.2.1)heptane-2-carboxylate (0.259 g), and diisopropylethylamine (0.622 mL) in acetonitrile (11.9 mL) was heated at 50° C. for 18 hours then cooled, diluted with dichloromethane, washed with saturated ammonium chloride and brine, and dried (MgSO4), filtered, and concentrated; and the concentrate was recrystallized from diethyl ether.

Workup

  1. temperaturethen cooled
  2. washwashed with saturated ammonium chloride and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customand the concentrate was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-96b50a1a551c4ff2a30e5e398edce182
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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