HCID 89689894, compound → HCID 131733357, compound

HRID 517911Notes

Reaction equation

HRID 517911 reaction equation
[OH:1][C:2]1([CH3:37])[C:7]2=[N:8][C:9]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:11]=[C:6]2[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:4][CH2:3]1.[CH3:38][O:39][C:40]1([CH3:75])[C:45]2=[N:46][C:47]([C:57]3[CH:62]=[CH:61][C:60]([CH3:63])=[CH:59][CH:58]=3)=[C:48]([C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)[N:49]=[C:44]2[N:43]([CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][C:70]([O:72][CH2:73][CH3:74])=[O:71])[CH2:42][CH2:41]1>CO>[CH3:38][O:39][C:40]1([CH3:75])[C:45]2=[N:46][C:47]([C:57]3[CH:62]=[CH:61][C:60]([CH3:63])=[CH:59][CH:58]=3)=[C:48]([C:50]3[CH:51]=[CH:52][C:53]([CH3:56])=[CH:54][CH:55]=3)[N:49]=[C:44]2[N:43]([CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][C:70]([O:72][CH2:73][CH3:74])=[O:71])[CH2:42][CH2:41]1.[OH:1][C:2]1([CH3:37])[C:7]2=[N:8][C:9]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:11]=[C:6]2[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 89689894HCID 89689894, compoundHCID 89690053HCID 89690053, compound

Product 1

HCID 131733357HCID 131733357, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-methyl-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-ol (Intermediate G)(240 mg, 0.695 mmol) in DCE (10 ml) was added ethyl 7-oxoheptanoate (359 mg, 2.084 mmol) followed by sodium triacetoxyborohydride (442 mg, 2.084 mmol) and the resulting mixture was left to stir overnight at room temperature under an atmosphere of nitrogen. The reaction mixture was diluted with water and extracted with EtOAc (2×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give a brown oil. The oil was purified by chromatography on silica eluting with EtOAc in iso-hexane to afford ethyl 7-(8-hydroxy-8-methyl-2,3-di-p-tolyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)heptanoate (Intermediate 15.1). This compound was passed through a 5 g Isolute® SCX-2 SPE cartridge (primed with MeOH—20 ml) and washing with MeOH (30 ml). The product was eluted with 2M NH3 in MeOH (20 ml). The basic eluent was concentrated under reduced pressure to afford a 1:2 mixture of ethyl 7-(8-hydroxy-8-methyl-2,3-di-p-tolyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)heptanoate compound: ethyl 7-(8-methoxy-8-methyl-2,3-d i-p-tolyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)heptanoate;

Workup

  1. washwashing with MeOH (30 ml)
  2. washThe product was eluted with 2M NH3 in MeOH (20 ml)
  3. concentrationThe basic eluent was concentrated under reduced pressure
  4. customto afford

Sources & evidence

ORD record
ord-befd6fad602e42ad9d93fc9960239dd3
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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