2,4-Dimethoxybenzylamine → HCID 25052214, compound

HRID 1685012Notes

Reaction equation

HRID 1685012 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]>O1CCCC1>[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 6) was taken up in tetrahydrofuran and an excess of the 2,4-dimethoxy-benzylamine (20 eq.) 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 using 0-8% gradient of 7 N ammonia/MeOH and DCM to give 1-(3,4-Dichloro-benzyl)-3-{4-[(2,4-dimethoxy-benzylamino)-methyl]-thiazol-2-yl}-urea.

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

Sources & evidence

ORD record
ord-60a9259a50764af89726c9c3a92eac9b
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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