L-Alaninol → (2S)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}propan-1-ol

HRID 1436362Notes

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]([CH3:18])[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]([CH3:18])[CH2:16][OH:17])[S:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-bromo-4-(4-bromophenyl)-1,3-thiazole (1.01 g, 3.16 mmol), prepared in step 2 of Example 1, and (S)-(+)-2-amino-1-propanol (738 μL, 9.48 mmol) was stirred under nitrogen at 150° C. for 1 h. After cooling to room temperature, the solid was taken up in methylene chloride and purified on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge) using a linear gradient of 10% ethyl acetate-methylene chloride to 40% ethyl acetate-methylene chloride as the eluent. Isolation of the more polar fraction gave (2S)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}propan-1-ol (415 mg, 42%) as a yellow oil; MS (ES) m/z 313.0 [M+H]+.

Workup

temperatureAfter cooling to room temperature
custompurified on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge)

Sources & evidence

ORD record: ord-9139153e9fc0493d8de3e01be55f5b15
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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