Ammonia → HCID 66631493, compound

HRID 1797930Notes

Reaction equation

HRID 1797930 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-])=O)=[CH:12][N:11]=1)[CH2:3][CH2:2]2.N>[Pd].CO>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([NH:16][C:13]1[CH:12]=[N:11][C:10]([N:4]2[CH:5]3[CH2:6][CH2:7][N:1]([CH2:9][CH2:8]3)[CH2:2][CH2:3]2)=[N:15][CH:14]=1)=[O:27]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66631377HCID 66631377, compound

Product 1

HCID 66631493HCID 66631493, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-yl]-2-nitro-benzamide (4.0 g, 9.9 mmol), palladium on carbon (100 mg, 10%) and methanol (100 ml) was stirred under hydrogen for 3 days. The mixture was neutralized by adding aqueous ammonia and extracted with chloroform. The mixture was dried and evaporated. The yellow oil was mixed with ethanol (25 ml) and hydrochloric acid (3 ml, 3 M). The mixture was cooled on an ice bath. The crystals were filtered and washed with ethanol followed by diethylether. Yield 2.27 g (61%).

Workup

  1. extractionextracted with chloroform
  2. customThe mixture was dried
  3. customevaporated
  4. additionThe yellow oil was mixed with ethanol (25 ml) and hydrochloric acid (3 ml, 3 M)
  5. temperatureThe mixture was cooled on an ice bath
  6. filtrationThe crystals were filtered
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-087f4a2feb9b418a913de4ea5841af11
Source dataset
uspto-grants-2013_01
Patent number
US08343960B2

Reaction notes

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