(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → HCID 66919011, compound

HRID 2354161Notes

Reaction equation

HRID 2354161 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:15]1([NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH3:40])=[C:25]([NH:27][C:28](=[O:39])[C:29]3[CH:34]=[C:33](F)[CH:32]=[CH:31][C:30]=3[N+:36]([O-:38])=[O:37])[CH:26]=2)=[O:20])[CH2:17][CH2:16]1>>[CH:15]1([NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH3:40])=[C:25]([NH:27][C:28]([C:29]3[CH:34]=[C:33]([N:5]4[CH2:6][C@@H:1]5[CH2:7][C@H:4]4[CH2:3][N:2]5[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:32]=[CH:31][C:30]=3[N+:36]([O-:38])=[O:37])=[O:39])[CH:26]=2)=[O:20])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 669189745-fluoro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide

Product 1

HCID 66919011HCID 66919011, compound

Procedure

Using an analogous procedure to that described paragraph (B) in the portion of Example 1, which is concerned with the preparation of starting materials, and tert-butyl(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate was reacted with N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide to give of tert-butyl(1S,4S)-5-{3-[({5-[(cyclopropylamino)carbonyl]-2-methylphenyl}amino)carbonyl]-4-nitrophenyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate; NMR Spectrum: (DMSOd6) 0.59 (m, 2H), 0.70 (m, 2H), 1.39 (d, 9H), 2.00 (m, 2H), 2.32 (s, 3H), 2.54 (s, 2H), 2.86 (m, 1H), 3.40 (m, 1H), 3.66 (t, 1H), 4.53 (d, 1H), 4.87 (s, 1H), 6.80 (s, 2H), 7.30 (d, 1H), 7.58 (m, 1H), 8.01 (s, 1H), 8.07 (d, 1H), 8.38 (d, 1H), 9.90 (s, 1H); Mass Spectrum: M+H+ 536.

Sources & evidence

ORD record
ord-c65b09ff045d4dd692c0725e7f702541
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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