Triethylamine → HCID 58622231, compound

HRID 2220721Notes

Reaction equation

HRID 2220721 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH2:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.[CH3:48][O:49][C:50]1[C:55]2[O:56][C:57]([CH3:60])([CH3:59])[O:58][C:54]=2[CH:53]=[C:52]([C:61](Cl)=[O:62])[CH:51]=1>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][N:26]([C:61]([C:52]1[CH:51]=[C:50]([O:49][CH3:48])[C:55]2[O:56][C:57]([CH3:60])([CH3:59])[O:58][C:54]=2[CH:53]=1)=[O:62])[CH2:11][C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 594088Quinoxaline-2-carbaldehydeHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 714100777-Methoxy-2,2-dimethyl-2H-1,3-benzodioxole-5-carbonyl chloride

Product 1

HCID 58622231HCID 58622231, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental conditions analogous Example 1, 0.12 g (0.81 mmol) of quinoxaline-2-carbaldehyde, 0.24 g (1.22 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, 5 mL dichloromethane, and 0.25 g (1.22 mmol) of sodium triacetoxyborohydride. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 40 min. Fractions containing pure product were evaporated in vacuum and dissolved in 3 mL dichloromethane. To this solution were added 0.34 mL (2.43 mmol) of triethylamine and 196 mg (0.81 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride. After 4 hours the reaction mixture was purified using flash chromatography (ethyl acetate in hexane), gave 280 mg as a yellow solid. LC-MSD, m/z for C30H36N4O6 [M+H]+: 549.7.

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customThe residue from the organic layer was purified
  3. customin 40 min
  4. additionFractions containing pure product
  5. customwere evaporated in vacuum
  6. dissolutiondissolved in 3 mL dichloromethane
  7. customAfter 4 hours the reaction mixture was purified
  8. customgave 280 mg as a yellow solid

Sources & evidence

ORD record
ord-81a758ceec0242e797533127f338dfc2
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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