反応 #71690

反応方程式

(3S)-3-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HATU

6-chloro-3-pyridinecarboxylic acid

DIPEA

→

title compound

収率 98.0%

(2S)-1-[(6-Chloro-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

収率 98.0%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 1.25 h
3. 3
   その他The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3 solution (20 ml each)
4. 4
   その他The layers were separated
5. 5
   洗浄the aqueous layer was washed with further DCM (2×20 ml)
6. 6
   濃縮The combined organic layers were concentrated
7. 7
   その他to leave a dark brown gum
8. 8
   その他Purification by silica chromatography (Biotage SP4, 25S cartridge)
9. 9
   洗浄eluting with 12-100% ethyl acetate in pentane

実験手順

HATU (458 mg, 1.21 mmol) was added to a solution of 6-chloro-3-pyridinecarboxylic acid (supplied by Aldrich) (174 mg, 1.10 mmol) in DMF (4 ml) and the mixture was treated with DIPEA (0.437 ml, 2.50 mmol). This mixture was stirred for ca. 10 min at ambient temperature. (3S)-3-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Description 2) (308 mg, 1.0 mmol) was added and stirring was continued for 1.25 h. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3 solution (20 ml each). The layers were separated and the aqueous layer was washed with further DCM (2×20 ml). The combined organic layers were concentrated to leave a dark brown gum. Purification by silica chromatography (Biotage SP4, 25S cartridge), eluting with 12-100% ethyl acetate in pentane, gave the title compound (439 mg) as a pale yellow gum.

出典