Ammonia → HCID 67058583, compound

HRID 470298Notes

Reaction equation

HRID 470298 reaction equation
[CH2:1]([N:3]1[CH2:32][CH2:31][C:5]2([CH2:9][N:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[C:20]4[CH:25]=[CH:24][C:23](F)=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4]1)[CH3:2].[NH3:33]>CN(C=O)C>[NH2:33][C:23]1[CH:24]=[CH:25][C:20]([C:19]([NH:18][C:15]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][N:8]3[CH2:7][CH2:6][C:5]4([CH2:31][CH2:32][N:3]([CH2:1][CH3:2])[CH2:4]4)[CH2:9]3)=[CH:17][CH:16]=2)=[O:30])=[CH:21][C:22]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67058578HCID 67058578, compound

Product 1

HCID 67058583HCID 67058583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{4-[2-(7-Ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-4-fluoro-3-nitro-benzamide from above was dissolved in DMF (15 ml) and the solution was cooled in an ice bath and saturated with ammonia gas for 10 min. The flask was sealed and left at room temperature overnight. The DMF was then evaporated under reduced pressure and the residue partitioned between dichloromethane and 0.1 N KOH. The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified on silica gel using 10% MeOH/CH2Cl2 1% TEA to afford 4-Amino-N-{4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-3-nitro-benzamide (996 mg) as a yellow foam which was used as is in the next step. 1H NMR (300 MHz, d6-DMSO) δ 10.2 (s, 1H), 8.70 (s, 1H), 7.96 (d, 1H), 7.82 (s, 2H), 7.63 (dd, 2H), 7.24 (dd, 2H), 7.10 (d, 1H), 2.65-2.35 (m, 14H), 1.96 (m, 4H), 1.23 (t, 3H).

Workup

  1. customThe flask was sealed
  2. customThe DMF was then evaporated under reduced pressure
  3. customthe residue partitioned between dichloromethane and 0.1 N KOH
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified on silica gel using 10% MeOH/CH2Cl2 1% TEA

Sources & evidence

ORD record
ord-9969f792192343079f6539f0761f7f9a
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…