1,2-Dichloroethane → HCID 58149347, compound

HRID 2407369Notes

Reaction equation

HRID 2407369 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[OH:32][C:33]12[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH:36]3[NH:43][CH3:44])[CH2:34]1)[CH2:40]2.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([N:43]([CH:36]2[CH:37]3[CH2:38][CH:39]4[CH2:40][C:33]([OH:32])([CH2:34][CH:35]2[CH2:41]4)[CH2:42]3)[CH3:44])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 37214804-(Methylamino)adamantan-1-olHCID 18544082HCID 18544082, compound

Product 1

HCID 58149347HCID 58149347, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

3-Cyclohexylmethoxy-benzoic acid (300 mg, 1.3 mmol), HOBT (294 mg, 1.9 mmol), EDC (245 mg, 1.3 mmol), and 1-hydroxy-4-methylaminoadamantane (232 mg, 1.28 mmol) were suspended in DMF (2.5 ml) before DIPEA (0.44 ml, 2.6 mmol) was added. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was purified directly by Preparative HPLC to give 199 mg of the title compound as a mixture of two isomers.

Workup

  1. additionwas added
  2. customThe reaction mixture was purified directly by Preparative HPLC

Sources & evidence

ORD record
ord-179bfac1e40042189d5dfcc835b696b5
Source dataset
uspto-grants-2014_08
Patent number
US08809540B2

Reaction notes

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