Acetic Acid → HCID 11951825, compound

HRID 1669069Notes

Reaction equation

HRID 1669069 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].[O-:10][N+:11]1[C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][C:15]=2[N:14]=[C:13]([CH2:24][CH2:25][CH:26]=O)[N:12]=1)[CH2:21][CH2:20][CH2:19]3.[BH3-]C#N.[Na+].CC(O)=O>CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][CH3:9])[CH2:26][CH2:25][CH2:24][C:13]1[N:12]=[N+:11]([O-:10])[C:16]2[CH:17]=[C:18]3[C:22]([CH2:21][CH2:20][CH2:19]3)=[CH:23][C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2383Bis(2-Methoxyethyl)amineHCID 5003444Sodium cyanoborohydrideHCID 57786560HCID 57786560, compound

Product 1

HCID 11951825HCID 11951825, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bis-(2-methoxyethyl)amine (3.0 g, 22.5 mmol) was added to a stirred solution of propanal 75 (1.2 g, 4.9 mmol) in MeOH (100 ml) at 0° C. and the solution stirred for 30 min. NaCNBH3 (1.5 g, 24 mmol) was added and the solution stirred at 0° C. for 30 min and then HOAc (2 mL) was added and the mixture was stirred at 20° C. for 16 h. The solvent was evaporated and the residue was partitioned between DCM (200 mL) and water (200 mL). The aqueous phase was extracted with DCM (2×200 ml), the combined organic phase was dried and the solvent evaporated. The residue was purified by chromatography, eluting with 10% MeOH/EtOAc, to give 1-oxide 80 (1.1 g, 50%) as a yellow oil: 1H NMR [(CD3)2SO] δ 8.19 (s, 1H, H-9), 7.83 (s, 1H, H-5), 3.61-3.68 (m, 4H, 2×CH2O), 3.31-3.38 (m, 4H, 2×CH2N), 3.26 (s, 6H, 2×OCH3), 3.20-3.14 (m, 4H, 2×CH2), 3.07-3.12 (m, 4H, H-6, H-8), 2.15-2.10 (m, 4H, H-7, CH2); 13C NMR δ 163.9, 154.7, 149.0, 146.7, 131.8, 122.2, 113.6, 58.0 (2), 57.4 (2), 52.4, 52.3, 32.5, 32.2, 25.3, 23.0 (2), 19.1; HRMS (FAB+) calcd for C19H29N4O3 (MH+) m/z 361.2240, found 361.2243.

Workup

  1. stirringthe solution stirred at 0° C. for 30 min
  2. stirringthe mixture was stirred at 20° C. for 16 h
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between DCM (200 mL) and water (200 mL)
  5. extractionThe aqueous phase was extracted with DCM (2×200 ml)
  6. customthe combined organic phase was dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-b45f764591574767b3db908a677e2781
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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