Ethanolamine → 1-(3-Fluorobenzyl)-3-(4-((2-hydroxyethylamino)methyl)thiazol-2-yl)urea

HRID 1685021Notes

Reaction equation

HRID 1685021 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[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].[NH2:20][CH2:21][CH2:22][OH:23].O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][NH:20][CH2:21][CH2:22][OH:23])[N:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea2×

Product 1

HCID 866612871-(3-Fluorobenzyl)-3-(4-((2-hydroxyethylamino)methyl)thiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate 7) was taken up in tetrahydrofuran and an excess of the 2-amino-ethanol (20 equiv.) was added. The reaction was allowed to stir overnight at room temperature. The reaction was poured into water and extracted with EtOAc, partitioned with brine, dried over Na2SO4, filtered, and volatiles were removed in vacuo. The resulting solid was triturated with EtOAc, followed by diethyl ether to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. custompartitioned with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customvolatiles were removed in vacuo
  6. customThe resulting solid was triturated with EtOAc

Sources & evidence

ORD record
ord-13de9e1de7f74a22b9250855c5dbfb0f
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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