Acetic Acid → HCID 21866231, compound

HRID 857791Notes

Reaction equation

HRID 857791 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[CH:14]=[N:13][S:12][N:11]=2)=[C:6]([CH:9]=1)[CH:7]=O.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[CH:14]=[N:13][S:12][N:11]=2)=[C:6]([CH:9]=1)[CH2:7][NH:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21866248HCID 21866248, compound

Product 1

HCID 21866231HCID 21866231, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 5-chloro-2-(1,2,5-thiadiazol-3-yl)benzaldehyde (0.155 g, 0.69 mmol), 4-methoxybenzylamine (0.09 mL, 0.69 mmol) and acetic acid (0.05 mL, 0.83 mmol) in 1,2-dichloroethane (5.2 mL) was added sodium triacetoxyborohydride (0.731 g, 3.45 mmol). The solution was stirred at ambient temperature for 16 h then partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The organic phase was dried (Na2SO4) and reduced in vacuo. The residue was purified by automated preparative chromatography on silica (eluting with 5% CH2Cl2/EtOAc/hexanes gradient, 5–50% EtOAc). N-[5-Chloro-2-(1,2,5-thiadiazol-3-yl)benzyl]-N-(4-methoxybenzyl)amine was isolated as an oil. 1H NMR (CDCl3, 400 MHz) δ 3.74 (s, 2H), 3.81 (s, 3H), 3.82 (s, 2H), 6.86 (d, J=8.6 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 8.84 (s,1H); MS m/z=346.5.

Workup

  1. customthen partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customThe residue was purified by automated preparative chromatography on silica (eluting with 5% CH2Cl2/EtOAc/hexanes gradient, 5–50% EtOAc)

Sources & evidence

ORD record
ord-164d33a5f8b74adcb76eaf20e2fba186
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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