Ammonium Hydroxide → HCID 9932698, compound

HRID 2307857Notes

Reaction equation

HRID 2307857 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]2[C:19]1[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[CH2:23][CH:24]=1)#[N:2].[OH-].[NH4+]>C(O)(=O)C.O=[Pt]=O>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH:7]=[C:6]2[CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 15006444HCID 15006444, compound

Product 1

HCID 9932698HCID 9932698, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

5-Cyano-1-(4-fluorophenyl)-3-[1-[2-(2-imidazolidinon-1-yl)ethyl]-1,2,3,6-tetrahydropyridin4-yl]-1H-indole (Perregaard, J.; Bges, K. P.; Hyttel, J.; Sánches, C.: J Med. Chem., 1992, 35, 1092-1101) (4.6 g) was hydrogenated with PtO2 in acetic acid at 3 ATO for 5 h. Ice and ammonium hydroxide was added to pH 9 and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and the solvent was removed in vacuo. The title compound was purified by preparative HPLC (ethanol/NH4OH 100/4). Yield 0.9 g, mp. 171-175° C. (diethyl ether). 1H-NMR (CDCl3) 1.85 (d, 2H), 2.10 (d, 2H), 2.25 (td, 2H), 2.60 (t, 2H), 2.90 (tt, 1H), 3.10 (d, 2H), 3.4 (q, 4H), 3.6 (q, 2H), 3.95 (s, 2H), 4.70 (s, broad, 1H), 7.00 (s, 1H), 7.10-7.25 (m, 3H), 7.30-7-50 (m, 3H), 7.60 (s, 1H). Analysis: Calc (corrected for 1% water): C: 68.22, H: 7.01, N: 15.92 Found: C: 67.51, H: 6.90, N: 15.37

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe title compound was purified by preparative HPLC (ethanol/NH4OH 100/4)

Sources & evidence

ORD record
ord-de80f607225d4a7891f3dbf6d1e2a878
Source dataset
uspto-grants-2004_12
Patent number
US06833376B2

Reaction notes

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