1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(3-Pyrid-4-ylpropionamido)-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

HRID 2217751Notes

Reaction equation

HRID 2217751 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][C:13]1[N:28]=[CH:27][C:16]2[N:17]([CH:24]([CH3:26])[CH3:25])[C:18]3[C:23]([C:15]=2[C:14]=1[CH2:29][CH3:30])=[CH:22][CH:21]=[CH:20][CH:19]=3.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39](O)=[O:40])=[CH:33][CH:32]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([NH:12][C:13]2[N:28]=[CH:27][C:16]3[N:17]([CH:24]([CH3:26])[CH3:25])[C:18]4[C:23]([C:15]=3[C:14]=2[CH2:29][CH3:30])=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:40])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2332433-(Pyridin-4-yl)propanoic acidHCID 693095793-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

Product 1

HCID 101107123-(3-Pyrid-4-ylpropionamido)-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

EDAC (0.035 g, 0.18 mmol) was added to a solution of 3-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 5; 0.03 g, 0.12 mmol), DMAP (0.007 g, 0.06 mmol) and 3-(pyridin-4-yl)propanoic acid (Method 6; 0.027 g, 0.18 mmol) in DMF (10 ml). The mixture was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane and a saturated solution of sodium bicarbonate. The organic layer was separated, washed with brine, dried over magnesium sulphate and then evaporated to dryness in vacuo. The crude product was purified by flash chromatography eluting over a gradient of 0-10% MeOH in DCM. NMR (CDCl3) 8.72 (s, 1H), 8.51 (m, 2H), 8.19 (d, 1H), 7.59 (d, 2H), 7.47 (s, 1H), 7.29 (m, 1H), 7.20 (m, 2H), 5.05 (m, 1H), 3.12 (m, 4H), 2.78 (m, 2H), 1.73 (d, 6H), 1.31 (t, 3H); m/z 388.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness in vacuo
  7. customThe crude product was purified by flash chromatography
  8. washeluting over a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-1dff5b50edfc4492bee75804c399c5ef
Source dataset
uspto-grants-2008_08
Patent number
US07408064B2

Reaction notes

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