Acetic Acid → HCID 25122337, compound

HRID 2382156Notes

Reaction equation

HRID 2382156 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[N:7]2.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(O)(=O)C>CN(C=O)C>[CH2:21]([N:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][NH:12][C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[N:11][C:2]=3[CH3:1])[N:7]=2)[CH2:16][CH2:17]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 2724942TriacetoxyborohydrideHCID 25121972HCID 25121972, compound

Product 1

HCID 25122337HCID 25122337, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 8 (56.74 mg, 0.136 mmol) in DMF (10 mL) was added benzaldehyde (21.65 mg, 0.204), MP-triacetoxyborohydride (2.70 mmol/g, 302 mg, 0.816 mmol), and acetic acid (24.5 mg, 0.408 mmol). It was stirred at room temperature overnight. The resin was removed by filtration. The solvent was removed and chromatography on silica gel afforded compound 9 (46.0 mg, 93.6). 1H NMR (CD3OD, 400 MHz) δ 8.19 (d, 1H, J=5.5 Hz), 8.09 (d, 1H, J=7.5 Hz), 7.20-7.35 (m, 6H), 6.81 (d, 1H, J=7.5 Hz), 3.62-3.71 (m, 2H), 3.55 (s, 2H), 2.75 (s, 3H), 2.45-2.70 (m, 10H). LCMS (EI) m/z 362 (M+1).

Workup

  1. customThe resin was removed by filtration
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-25357bb9be63471c875e2168f2c5c550
Source dataset
uspto-grants-2012_09
Patent number
US08258301B2

Reaction notes

Loading…