2-Amino-2-methyl-1-propanol → 2-{[4-(4-Bromo-2-fluorophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol

HRID 1436414Notes

Reaction equation

HRID 1436414 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=2[F:14])[N:6]=1.[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18]>>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18])[S:3][CH:4]=2)=[C:8]([F:14])[CH:9]=1

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 689032302-Bromo-4-(4-bromo-2-fluorophenyl)-1,3-thiazole

Product 1

HCID 866186062-{[4-(4-Bromo-2-fluorophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-olYield 22%

Conditions

Temperature
175 °C

Procedure

2-Bromo-4-(4-bromo-2-fluorophenyl)-1,3-thiazole (1.5 g, 4.4 mmol), prepared in the previous step, and 2-amino-2-methyl-1-propanol (2.5 mL, 26.7 mmol) were placed in a sealed tube and heated to 175° C. overnight. The reaction was concentrated under reduced pressure. The residue was purified on silica gel using a stepwise gradient of 5-40% ethyl acetate:hexane to give 2-{[4-(4-bromo-2-fluorophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (0.3 g, 22%), MS (ES) m/z 346 [M+H]+.

Workup

  1. customwere placed in a sealed tube
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customThe residue was purified on silica gel using a stepwise gradient of 5-40% ethyl acetate

Sources & evidence

ORD record
ord-57dc58e43423447ab32c56b5920626b0
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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