HCID 86606903, compound → 4-Amino-5-cyano-N-[(2,5-dimethoxyphenyl)methyl]-6-(1-methylethoxy)-2-pyridinecarboxamide

HRID 1364536Notes

Reaction equation

HRID 1364536 reaction equation
[N:1]([C:4]1[C:9]([C:10]#[N:11])=[C:8]([O:12][CH:13]([CH3:15])[CH3:14])[N:7]=[C:6]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])=[O:17])[CH:5]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C:4]1[C:9]([C:10]#[N:11])=[C:8]([O:12][CH:13]([CH3:15])[CH3:14])[N:7]=[C:6]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])=[O:17])[CH:5]=1

Participants

4

Reactant 1

HCID 86606903HCID 86606903, compound

Product 1

HCID 498309314-Amino-5-cyano-N-[(2,5-dimethoxyphenyl)methyl]-6-(1-methylethoxy)-2-pyridinecarboxamideYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The azide from Example 102C (10 mg, 0.025 mmol) was hydrogenated in MeOH under a hydrogen balloon with cat. 10% Pd/C for 1 hour. The reaction mixture was filtered through a celite plug and washed with MeOH. The combined filtrate was evaporated and pumped in vacuo to provide the titled compound as a white solid (9.3 mg, 100% yield). 1H NMR (300 HZ, DMSO-d6) δ 8.81 (t, J=6.3 Hz, 1H), 7.30 (broad s, 2H), 7.04 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 6.79 (dd, J=8.8, 3.1 Hz, 1H), 6.71 (d, J=3.1 Hz, 1H), 5.53 (quintet, J=6.4 Hz, 1H), 4.41 (d, J=6.4 Hz, 2H), 3.79 (s, 3H), 3.65 (s, 3H), 1.31 (d, J=6.4 Hz, 6H). MS (m/e) 371 (M+H)+, 393 (M+Na)+.

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washwashed with MeOH
  3. customThe combined filtrate was evaporated

Sources & evidence

ORD record
ord-77f3954a7fa043f2ac833dba885cdc0b
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

Loading…