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

HRID 406187Notes

Reaction equation

HRID 406187 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.O=[CH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[C:1]1([C:7]2[N:12]=[C:11]3[N:13]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 666659633-Phenyl-2-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Product 1

HCID 66666309Ethyl 7-(3-phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

3-Phenyl-2-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate F) (162 mg, 0.538 mmol) in dry DCE (1 ml) was treated with DIPEA (0.103 ml, 0.591 mmol) followed by ethyl 7-oxoheptanoate (185 mg, 1.075 mmol). The reaction mixture was stirred at RT for 10 minutes and sodium triacetoxyborohydride (570 mg, 2.69 mmol) was added. The resulting mixture was stirred at 60° C. for 16 hours. 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 0-10% EtOAc/iso-hexane to afford the title compound; LCMS; Rt 1.38 mins MS m/z 458 [ M+H]+; Method 2minLC_v003

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 16 hours
  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 0-10% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-59133dd5ecab466babd93e6714bd0164
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

Loading…