2,4-Dimethoxybenzylamine → HCID 25052214, compound

HRID 1020263Notes

Reaction equation

HRID 1020263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]I)[N:14]=1)=[O:8].[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][NH:26][CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:23]=2[O:22][CH3:21])[N:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 58055059HCID 58055059, compound2×

Product 1

HCID 25052214HCID 25052214, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,4-dichlorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate XXII) was taken up in THF and an excess of the 2,4-dimethoxy-benzylamine (20 equiv.) was added. The reaction was allowed to stir overnight at room temperature. The volatiles were removed in vacuo. Resulting oil triturated with water to give a gooey solid. Water was decanted off and resulting residue was purified by column chromatography (DCM, 0-8% MeOH saturated with NH3). 1H NMR (400 MHz, CDCl3): 7.32 (d, 1H), 7.19 (br s, 1H), 7.01 (br d, 1H), 6.96 (d, 1H), 6.60 (s, 1H), 6.40-6.33 (m, 2H), 4.11 (br s, 2H), 3.78 (s, 3H), 3.71 (s, 3H), 3.69 (br s, 2H), 3.55 (br s, 3H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customResulting oil
  3. customtriturated with water
  4. customto give a gooey solid
  5. customWater was decanted off
  6. customresulting residue
  7. customwas purified by column chromatography (DCM, 0-8% MeOH saturated with NH3)

Sources & evidence

ORD record
ord-1ecfbbe89cc843b38ef2fbdcbc69cc91
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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