(2R)-2-aminopentan-1-ol → HCID 86618495, compound

HRID 493971Notes

Reaction equation

HRID 493971 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][CH:8]=2)[N:6]=1.[NH2:14][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:16][OH:17]>C(Cl)Cl>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:14][C@H:15]([CH2:18][CH2:19][CH3:20])[CH2:16][OH:17])[S:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5324727(2R)-2-aminopentan-1-olHCID 685381612-Bromo-4-(4-bromo-phenyl)-thiazole

Product 1

HCID 86618495HCID 86618495, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromo-4-(4-bromophenyl)-1,3-thiazole (2.9 g, 9.09 mmol), prepared in step 2 of Example 1, and (R)-(−)-2-amino-pentanol (2.82 g, 27.2 mmol) was stirred under nitrogen at 150° C. for 18 h. After cooling to room temperature, the residue was taken up in methylene chloride, applied to a Biotage FLASH 40+™ cartridge and the methylene chloride allowed to evaporate. Purification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge) using a linear gradient of 5% ethyl acetate-hexane to 100% ethyl acetate gave (2R)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}pentan-1-ol (2.56 g, 83%) as a yellow solid, mp 63-65° C.; MS (ESI) m/z 341 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customto evaporate
  3. customPurification of the residue on the samplet on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge)

Sources & evidence

ORD record
ord-f6b4c6a0d5ca41188558e370445d8d8c
Source dataset
uspto-grants-2009_05
Patent number
US07538107B2

Reaction notes

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