1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25145196, compound

HRID 390785Notes

Reaction equation

HRID 390785 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[NH2:48][CH:49]1[CH:56]2[CH2:57][C:52]3([OH:59])[CH2:53][CH:54]([CH2:58][CH:50]1[CH2:51]3)[CH2:55]2>CN(C=O)C>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8]([NH:48][CH:49]1[CH:50]2[CH2:58][CH:54]3[CH2:53][C:52]([OH:59])([CH2:57][CH:56]1[CH2:55]3)[CH2:51]2)=[O:10]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28574474-Aminoadamantan-1-olHCID 65248306HCID 65248306, compound

Product 1

HCID 25145196HCID 25145196, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(2,4-dichloro-phenoxy)-2,2-dimethyl-butyric acid (250 g, 0.902 mmol, prepared in a similar way as described in J. Am. Chem. Soc. 89, 2500-1 (1967)) in dry DMF (3 mL) was added HOBt (180 mg, 1.173 mmol) and EDAC (225 mg, 1.173 mmol). After stirring for 1 hr at room temperature, DIPEA (306 μL) and 4-amino-adamantan-1-ol (181 mg, 1.082 mmol) were added and the resulting mixture was stirred for 16 hrs. at room temperature. The volatiles were removed in vacuo and the residue was purified using prep. HPLC/MS affording 153 mg (40%) of the title compound as a solid. 1H NMR (400 MHz, CDCl3) □ 1.34 (s, 6H), 1.52 (q, 4H), 1.69-1.79 (m, 4H), 1.87 (d, 2H), 2.02-2.16 (m, 5H), 2.57 (br.s., 1H), 3.95-4.02 (m, 1H), 4.05 (t, 2H), 6.02 (d, 1H), 6.83 (d, 1H), 7.17 (dd, 1H), 7.35 (d, 1H).

Workup

  1. stirringthe resulting mixture was stirred for 16 hrs
  2. customat room temperature
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified

Sources & evidence

ORD record
ord-55cbfb76fd17444cb7d0d6b7ce04a4bb
Source dataset
uspto-grants-2013_02
Patent number
US08383683B2

Reaction notes

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