Cycloheptylamine → 1-Cycloheptyl-3-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 715134Notes

Reaction equation

HRID 715134 reaction equation
C=C([O:4][C:5](=O)[NH:6][C:7]1[CH:12]=[C:11]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[CH:10]=[CH:9][C:8]=1[F:22])C.[CH:24]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN1CCCC1>C1COCC1>[CH:24]1([NH:31][C:5]([NH:6][C:7]2[CH:12]=[C:11]([B:13]3[O:14][C:15]([CH3:21])([CH3:20])[C:16]([CH3:19])([CH3:18])[O:17]3)[CH:10]=[CH:9][C:8]=2[F:22])=[O:4])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 2899CycloheptylamineHCID 84541-MethylpyrrolidineHCID 89827739Prop-1-en-2-yl (2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Product 1

HCID 898158041-Cycloheptyl-3-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Treat a solution of prop-1-en-2-yl(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (0.460 g, 1.432 mmol) in THF (5 mL) with cycloheptylamine (0.195 g, 1.719 mmol) followed by a catalytic amount of 1-methylpyrrolidine (0.012 g, 0.143 mmol) and heat at 60° C. for 2 h. Concentrate the mixture to dryness, add MeCN, collect the solid via filtration and dry to afford the title compound (420 mg, 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.50 (dd, J=9, 1.7 Hz, 1H), 8.33 (s, 1H), 7.16 (m, 2H), 6.60 (d, J=7.0 Hz, 1H), 3.64 (m, 1H), 1.80 (m, 2H), 1.50 (m, 10H), 1.26 (s, 12H); MS(ESI) m/z: 377.2 (M+H+).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. additionadd MeCN
  3. customcollect the solid
  4. filtrationvia filtration
  5. customdry

Sources & evidence

ORD record
ord-f941602b8a8042a0826ce9288115f69b
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…