反応 #1488007

反応方程式

NaBH(OAc)3

(S)-4-amino-2-(tert-butoxycarbonylamino)butanoic acid

acetic acid

47

1-cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

→

title compound 107

収率 37.3%

(S)-tert-butyl 1-((6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]-pyridin-2-yl)pyridin-3-yl)methyl)-2-oxopyrrolidin-3-ylcarbamate

収率 37.3%

溶媒

DCM

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 16 h
2. 2
   その他quenched by addition of 1N NaOH
3. 3
   濃縮concentrated
4. 4
   ろ過The solid was collected by filtration
5. 5
   その他purified by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV)

実験手順

To a suspension of 47 (230 mg, 0.51 mmol, scheme 15) in DCM (5.1 mL) were added (S)-4-amino-2-(tert-butoxycarbonylamino)butanoic acid (224 mg, 1.03 mmol) and acetic acid (59 μl, 1.03 mmol). After stirring for 20 min at room temperature, NaBH(OAc)3 (326 mg, 1.54 mmol) was added. The reaction mixture was stirred for 16 h, quenched by addition of 1N NaOH, and concentrated. The solid was collected by filtration and purified by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV), to afford the title compound 107 (120 mg, 0.19 mmol, 37% yield). MS (m/z): 633.7 (M+H).

出典