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

HRID 406191Notes

Reaction equation

HRID 406191 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]=1.CCN(C(C)C)C(C)C.O=[CH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[C:1]1([CH3:24])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 666663642-m-Tolyl-3-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 66665344Ethyl 7-(2-m-tolyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

2-m-Tolyl-3-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate FB)(61 mg, 0.193 mmol) in dry DCE (1 ml) at RT was treated with DIPEA (0.037 ml, 0.213 mmol) followed by ethyl 7-oxoheptanoate (66.6 mg, 0.387 mmol). The reaction mixture was stirred at RT for 10 minutes and sodium triacetoxyborohydride (205 mg, 0.967 mmol) was added. The resulting mixture was stirred at 60° C. overnight. After cooling to RT, the mixture was slowly added to water (50 ml) and extracted with DCM (3×). The combined organic extracts were passed through a phase separating column and concentrated in vacuo. The resulting crude product was purified by chromatography on silica eluting with 0-5% EtOAc/iso-hexane to afford the title compound; LCMS Rt 1.61 mins MS m/z 473.4 [ M+H]+; Method 2minLC_v003

Workup

  1. stirringThe resulting mixture was stirred at 60° C. overnight
  2. temperatureAfter cooling to RT
  3. extractionextracted with DCM (3×)
  4. customseparating column
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by chromatography on silica eluting with 0-5% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-406927cd40aa416185ff3b030502ca90
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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