Tetrahydrofuran → HCID 58997052, compound

HRID 251156Notes

Reaction equation

HRID 251156 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.O(C([CH2:36][O:37][NH2:38])=O)C1C=CC=CC=1.C1C[O:42][CH2:41]C1>>[CH3:36][O:37][NH:38][C:41]([N:14]1[CH2:15][CH2:16][CH:11]([N:10]([CH2:9][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=2)[CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:12][CH2:13]1)=[O:42]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 45091051HCID 45091051, compoundHCID 58997074(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58997052HCID 58997052, compound

Procedure

(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine (125 mg, 0.36 mmol) and N-(phenoxycarbonyl)methoxylamine (120 mg, 0.71 mmol) were stirred in THF (3.5 mL) for 16 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography with silica gel (20:1:0.2 CH2Cl2/MeOH:NH4OH), COMPOUND 300 as a sticky solid (110 mg, 72%). 1H NMR (CDCl3) δ 0.93 (d, 6H, J=6.9 Hz), 1.62 (dq, 2H, J=12.3, 3.8 Hz), 1.89 (br d, 2H, J=12.3 Hz), 2.16 (s, 3H), 2.28 (s, 3H), 2.64 (br t, 2H, J=12.3 Hz), 2.74 (m, 1H), 2.78 (sept, 1H, J=6.9 Hz), 3.71 (s, 3H), 3.77 (s, 2H), 3.82 (s, 2H), 4.02 (br d, 2H, J=12.0 Hz), 7.13 (br, 1H(NH)), 7.16 (m, 1H), 7.24 (s, 1H), 7.50 (d, 1H, J=7.2 Hz), 8.18 (s, 1H), 8.32 (d, 1H, J=3.9 Hz). 13C NMR (CDCl3) δ 18.30, 18.45, 23.59 (2C), 27.30 (2C), 27.38, 44.40 (2C), 54.35 (2C), 57.24, 64.49, 123.20, 132.30, 133.23, 133.88, 139.09, 144.42, 146.05, 146.63, 154.42, 156.24, 159.06. ES-MS m/z 426 (M+H). Anal. Calcd. for C24H35N5O2.0.3CH2Cl2: C, 64.71; H, 7.96; N, 15.53. Found: C, 64.94; H, 8.09; N, 15.88.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography with silica gel (20:1:0.2 CH2Cl2/MeOH:NH4OH), COMPOUND 300 as a sticky solid (110 mg, 72%)

Sources & evidence

ORD record
ord-1c9c94fa8e764f45890e8cb572de5795
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…