Trifluoroacetic acid → HCID 21462996, compound

HRID 1940562Notes

Reaction equation

HRID 1940562 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][N:18]2[CH2:23][CH:22]=[C:21](/[CH:24]=[CH:25]/[C:26]3[O:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[CH2:20][CH2:19]2)=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[NH4+]>ClCCl>[CH3:31][C:28]1[O:27][C:26](/[CH:25]=[CH:24]/[C:21]2[CH2:22][CH2:23][N:18]([CH2:17][C:10]3[C:11]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:8][CH:9]=3)[CH2:19][CH:20]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 21463001HCID 21463001, compound

Product 1

HCID 21462996HCID 21462996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-1-tert-butyloxycarbonyl-3-(4-[2-(5-methylfuran-2-yl)ethenyl]-1,2,3,6-tetrahydropyridin-1-yl)methylpyrrolo[2,3-b]pyridine (160 mg, 0.38 mmol) in anhydrous dichloromethane (5 ml) was treated with trifluoroacetic acid (500 ml, 6.5 mmol) and stirred at room temperature for two hours. Ammonium hydroxide solution (5 ml) was added and the whole mixture evaporated in vacuo. The residue was azeotroped with toluene. The crude material was chromatographed on silica gel with 5% methanol in dichloromethane as eluant to afford the title compound as a pale lemon solid (70 mg, 57%), m.p. 180° C. (dec.); (Found: C, 71.47; H, 6.46; N, 12.01. C20 H21N3O.H2O requires C, 71.19; H, 6.87; N, 12.42%); δH (DMSO-d6) 2.15-2.30 (5H, m, tetrahydropyridinyl CH2 and ArCH3), 2.59 (2H, t, J 5.5 Hz, tetrahydropyridinyl CH2), 3.02-3.10 (2H, m, tetrahydropyridinyl CH2), 3.71 (2H, s, NCH2Ar), 5.78-5.86 (1H, m, tetrahydropyridinyl 5-H), 6.05-6.10 (1H, m, furan 4-H), 6.16-6.30 (2H, m, CH=CHAr and furan 3-H), 6.55 (1H, d, J 16.1 Hz, CH=CHAr), 7.02 (1H, dd, J 7.8, 4.8 Hz, 5-H), 7.34-7.38 (1H, m, 2-H), 8.01 (1H, d, J 7.8 Hz, 4-H), 8.18 (1H, d, J 4.6 Hz, 6-H), and 11.45 (1H, s, NH); m/z (CI+, NH3) 320 (M+1)+.

Workup

  1. customthe whole mixture evaporated in vacuo
  2. customThe residue was azeotroped with toluene
  3. customThe crude material was chromatographed on silica gel with 5% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-4d67494eefb24ec1a046341cc186b218
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

Loading…