Ammonium Hydroxide → HCID 178512339, compound

HRID 343335Notes

Reaction equation

HRID 343335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:43])[CH2:25][CH:26]4[CH2:31][CH2:30][N:29]([C:32](=[N:40][C:41]#[N:42])OC5C=CC=CC=5)[CH2:28][CH2:27]4)[CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1.[OH-].[NH4+:45]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:43])[CH2:25][CH:26]4[CH2:31][CH2:30][N:29]([C:32](=[NH:45])[NH:40][C:41]#[N:42])[CH2:28][CH2:27]4)[CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 15840849HCID 15840849, compound2×

Product 1

HCID 178512339HCID 178512339, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

Phenyl 4-[2-[4-(3-bromo-8-chloro-6,11-dihydro-5 H-benzo[5,6] cyclohepta[1,2-b]pyridin-11-yl)-1-piperazinyl]-2-oxoethyl]-N-cyano-1-piperidinecarboximidate (2.62 g) (Formula 2.0, prepared as described in Example 1 above) was dissolved in 2-propanol (50 ml) and concentrated ammonium hydroxide (4 ml) was added. The mixture was stirred at 25° C. for 24 h and then evaporated to dryness. The residue was triturated with diethyl ether (2×250 ml) and the ether was discarded. The remaining product was chromatographed on a silica gel column (60×2.5 cm) using 4% (10% concentrated ammonium hydroxide in methanol)-dichloromethane as the eluant to give the title compound (Formula 3.0) (1.967 g;85%), FABMS: m/z 584.2 (MH+).

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with diethyl ether (2×250 ml)
  3. customThe remaining product was chromatographed on a silica gel column (60×2.5 cm)

Sources & evidence

ORD record
ord-02bf78ecb0f141369b8fcc9c74a489f6
Source dataset
uspto-grants-1999_01
Patent number
US05861395

Reaction notes

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