1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66954283, compound

HRID 1424618Notes

Reaction equation

HRID 1424618 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12](O)=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][NH2:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([CH:18]=[C:17]([O:16][CH3:15])[CH:22]=1)[CH2:25][NH:26][C:12]([C:5]12[CH2:4][CH:3]3[CH2:11][CH:7]([CH2:8][CH:9]([C:2]3=[O:1])[CH2:10]1)[CH2:6]2)=[O:13]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 28425154-Oxoadamantane-1-carboxylic acid

Product 1

HCID 66954283HCID 66954283, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-oxoadamantane-1-carboxylic acid (200 mg, 1.03 mol), (3,5-dimethoxyphenyl)methanamine (172 mg, 1.03 mmol), EDCI (410 mg, 2.06 mmol), and HOBt (280 mg, 2.06 mmol) were dissolved in dry CH2Cl2. DIEA (1.3 g, 10 mmol) was added under nitrogen at 0° C. and the mixture was stirred overnight at rt. The mixture was washed with water and brine. The organic layer was dried and concentrated to give crude product which was purified by preparative TLC to give N-(3,5-dimethoxybenzyl)-4-oxoadamantane-1-carboxamide (231 mg, 65%). 1H NMR: (400 MHz, CDCl3): δ=1.62 (s, 4H) 1.95-2.25 (m, 13H), 2.59 (s, 2H), 3.78 (s, 3H), 3.83 (s, 3H), 4.35 (d, 2H), 6.05 (s, 1H), 6.44 (m, 2H), 7.15 (d, 1H).

Workup

  1. washThe mixture was washed with water and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give crude product which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-e6618c783ff0478e83b09c2977dd898f
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…