反応 #218062

反応方程式

6-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide

K2CO3

isoamyl bromide

→

title compound

収率 72.0%

6-[2-(3-Methylbutyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy]nicotinamide

収率 72.0%

溶媒

DMF

反応条件

後処理

1. 1
   洗浄Pass through an SCX column, washing with methanol
2. 2
   洗浄eluting with 2.0 M NH3 in MeOH
3. 3
   濃縮Concentrate the eluant
4. 4
   その他purify by flash chromatography
5. 5
   洗浄eluting with 70:22:8 EtOAc/CH2Cl2/2.0 M NH3 in MeOH

実験手順

Mix 6-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide (Example 447, Part E, 50.7 mg, 0.18 mmol), K2CO3 (49.5 mg, 0.36 mmol), and isoamyl bromide (32 uL, 0.27 mmol) in DMF (1.0 mL). Heat at 80° C. for 6 hours. Pass through an SCX column, washing with methanol and then eluting with 2.0 M NH3 in MeOH. Concentrate the eluant and purify by flash chromatography, eluting with 70:22:8 EtOAc/CH2Cl2/2.0 M NH3 in MeOH to afford the title compound (45.7 mg, 72%): MS ES+ 354.0 (M+H)+, HRMS calcd for C21H28N3O2 354.2182 (M+H)+, found 354.2182, time 0.39 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=6.39 min, 100% purity; Anal. Calcd for C21H27N3O2.0.2CH2Cl2.0.1MeOH: C, 69.59; H, 5.98; N, 11.43. Found: C, 69.47; H, 6.25; N, 11.30.

出典