HCID 67426937, compound → HCID 59300994, compound

HRID 2235419Notes

Reaction equation

HRID 2235419 reaction equation
[CH3:1][C:2]1([CH3:35])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[N:4]([CH2:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:3]1=[O:34]>[Ni]>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2[NH:11][C:8]3=[CH:9][C:10]4[C:2]([CH3:35])([CH3:1])[C:3](=[O:34])[N:4]([CH2:25][CH2:26][CH2:27][N:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)[C:5]=4[CH:6]=[C:7]3[N:22]=2)=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 67426937HCID 67426937, compound

Product 1

HCID 59300994HCID 59300994, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
100 °C

Procedure

2-(4-Methoxy-phenyl)-7,7-dimethyl-5-(3-morpholin-4-yl-propyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one is prepared from N-[3,3-dimethyl-1-(3-morpholin-4-yl-propyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide (575 mg) by hydrogenation at 70° C. as described in Example 1b using Raney-nickel (70 mg). The catalyst is filtered off and the filtrate is heated at 100° C. for 2 h. By adding concentrated ammonia the desired compound (360 mg) precipitates and is collected by filtration.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionBy adding concentrated ammonia the desired compound (360 mg)
  3. customprecipitates
  4. filtrationis collected by filtration

Sources & evidence

ORD record
ord-819f54ec8cea4bec9f17799daa1b10f4
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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