Triethylamine → 1-{2-[{6-[(5-Bromopyrimidin-2-yl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446516Notes

Reaction equation

HRID 446516 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:36])[O:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]([C:28](=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH3:27])[CH2:20][CH2:19]1.C(N(CC)CC)C>C(O)CCC>[C:9]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:36])[O:17][CH:18]1[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][N:26]([C:28](=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH3:27])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 666715721-{2-[(6-Aminohexanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 666715871-{2-[{6-[(5-Bromopyrimidin-2-yl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamateYield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5-Bromo-2-chloropyrimidine (124 mg, 0.643 mmol) and the compound (300 mg, 0.643 mmol) obtained in Example 1a were dissolved in n-butanol (5 mL), triethylamine (0.134 mL, 0.965 mmol) was added, and the mixture was stirred with heating to reflux for 19 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→0:100, v/v) to give the title compound (299 mg; yield, 75%) as a yellow solid.

Workup

  1. temperaturewith heating
  2. temperatureto reflux for 19 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→0:100, v/v)

Sources & evidence

ORD record
ord-16a950ad5c69432ab157cf2d8687cc70
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

Loading…