Heptanoic acid, 7-oxo-, ethyl ester → Ethyl 7-(7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 517908Notes

Reaction equation

HRID 517908 reaction equation
[N:1]1([CH:7]2[CH2:30][NH:29][C:10]3=[N:11][C:12]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=[CH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[N:1]1([CH:7]2[CH2:30][N:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:10]3=[N:11][C:12]([C:22]4[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=4)=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 896900517-(Piperidin-1-yl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 89690354Ethyl 7-(7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(piperidin-1-yl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (step 7) (62 mg, 0.156 mmol) in DCE (5 ml) under nitrogen, was treated with ethyl 7-oxoheptanoate (53.6 mg, 0.311 mmol) and stirred at room temperature for 15 minutes. Sodium triacetoxyborohydride (132 mg, 0.622 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM (20 ml) and washed with water. The organic portion was passed through a phase separating column and concentrated under reduced pressure. Purification of the crude material by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with water
  3. customseparating column
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the crude material by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-ae05617cb9024efeaba1011d26c50c70
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

Loading…