تفاعل #577473

معادلة التفاعل

sodium hydrogen carbonate

( D4 )

1-(3-Methyl-isoquinolin-5-yl)-3-pyrrolidin-3-yl urea

2-trifluoromethyl benzaldehyde

isocyanate

Sodium triacetoxyborohydride

→

title compound

المردود 57.5%

1-(3-Methyl-isoquinolin-5-yl)-3-[1-(2-trifluoromethyl-benzyl)pyrrolidin-3-yl]urea

المردود 57.5%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction stirred for 48 h
2. 2
   workup.STIRRINGthe mixture stirred for 15min
3. 3
   أخرىThe organic layer was removed
4. 4
   workup.STIRRINGstirred with polymer
5. 5
   أخرىfor 3 h
6. 6
   ترشيحfiltered
7. 7
   غسيلeluted with methanol
8. 8
   أخرىEvaporation of the solvent in vacuo

الإجراء التجريبي

A mixture of (D4) (40 mg, 0.15 mmol) and 2-trifluoromethyl benzaldehyde (23 mg, 0.13 mmol) in dichloromethane (5 ml) was stirred at 25° C. for 1 h. Sodium triacetoxyborohydride (32 mg, 0.15 mmol) was added and the reaction stirred for 48 h. A saturated solution of sodium hydrogen carbonate (5 mL) was added and the mixture stirred for 15min. The organic layer was removed, stirred with polymer supported isocyanate resin (2.1 eq.) for 3 h and then filtered. The filtrate was applied to an SCX column and eluted with methanol followed by 2% ammonia in methanol. Evaporation of the solvent in vacuo gave the title compound as a pale yellow solid (32 mg, 56%). 1H NMR (CDCl3) δ: 2.25-2.35 (2H, m), 2.50-2.70 (3H, m), 2.62 (3H, s), 2.80-2.90 (1H, m), 3.67-3.75 (2H, m), 4.30-4.40 (1H, m), 5.35 (1H, d, J=8.1 Hz), 7.25-7.40 (3H, m), 7.45-7.55 (4H, m), 7.70-7.80 (2H, m), 9.16 (1H, s); MS: C23H23N4OF3 requires 428, found 429 (MH+).

المصدر