Ammonium Chloride → HCID 86726617, compound

HRID 1506164Notes

Reaction equation

HRID 1506164 reaction equation
O[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([OH:14])=O)([CH2:5]3)[CH2:3]1)[CH2:9]2.Cl.CN(C)CCCN=C=NCC.[OH:27]N1C2C=CC=CC=2N=N1.Cl.[CH3:38][NH:39][O:40][CH3:41].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>ClCCl.CN(C)C1C=CN=CC=1>[OH:27][C:2]12[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][C:4]([C:12]([N:39]([O:40][CH3:41])[CH3:38])=[O:14])([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

9

Reactant 6

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365183-Hydroxyadamantane-1-carboxylic acid

Product 1

HCID 86726617HCID 86726617, compoundYield 135.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

3-Hydroxyadamantane-1-carboxylic acid (500 mg, 2.55 mmol) in dichloromethane (15 mL) was mixed with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (587 mg, 3.06 mmol), 1-hydroxybenzotriazole (103 mg, 0.765 mmol), N,O-dimethylhydroxylamine hydrochloride (298 mg, 3.06 mmol) and N,N-diisopropylethylamine (1.06 mL, 6.12 mmol) and then stirred at 40° C. for 2 hours. The reaction mixture was stirred with 4-dimethylaminopyridine (779 mg, 6.38 mmol) at 40° C. for 2 hours. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with chloroform. The organic layer was washed with 1M hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a yellow oil (248 mg, yield 41%).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe organic layer was washed with 1M hydrochloric acid and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed72f1912b244b4ca6dfb040d8ac4ace
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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