Methanol → HCID 21906628, compound

HRID 1883032Notes

Reaction equation

HRID 1883032 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[C:14](I)[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[O:19])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:37][OH:38].CN(C)[CH:41]=[O:42]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[C:14]([C:37]([O:42][CH3:41])=[O:38])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 21906277N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide

Product 1

HCID 21906628HCID 21906628, compoundYield 38%

Conditions

Temperature
60 °C

Procedure

To a stirring solution of N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide (0.49 g, 0.92 mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (0.4 mL, 2.8 mmol), followed by PdCl2 (PPh3)2, and then methanol 15 mL). The mixture was placed under a carbon monoxide atmosphere, heated to 60° C. for 18 h, and concentrated in vacuo. The crude product was purified by chromatography over silica gel, eluting with a step gradient of 10-20% 2 M solution of ammonia/methanol in dichloromethane. The chromatography product was recrystallized from methanol to give 0.16 g (38%) of a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by chromatography over silica gel
  3. washeluting with a step gradient of 10-20% 2 M solution of ammonia/methanol in dichloromethane
  4. customThe chromatography product was recrystallized from methanol

Sources & evidence

ORD record
ord-7402dc3209f94976b2ff072889da93ba
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

Loading…