Amantadine → HCID 69225165, compound

HRID 2223232Notes

Reaction equation

HRID 2223232 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([C:19](O)=[O:20])[CH:13]=3)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:44]12([NH2:54])[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]3)[CH2:45]1)[CH2:51]2>O.CCN(CC)CC.CN(C=O)C>[C:44]12([NH:54][C:19]([C:14]3[CH:13]=[C:12]4[C:17]([CH:18]=[C:10]([C:7]5[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=5)[NH:11]4)=[CH:16][CH:15]=3)=[O:20])[CH2:51][CH:50]3[CH2:49][CH:48]([CH2:47][CH:46]([CH2:52]3)[CH2:45]1)[CH2:53]2

Participants

8

Reactant 4

HCID 2130AmantadineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 692257692-(4-Nitrophenyl)-1H-indole-6-carboxylic acid

Product 1

HCID 69225165HCID 69225165, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To an oven dried Argon cooled 100 mL flask, 605 mg acid 6, 493 mg EDCI.HCl, 348 mg of HOBt were added. While under Argon atmosphere, 30 mL of dry DMF and 1.79 mL of Et3N were added and the mixture was stirred at room temperature for 15 min. After this, 389 mg of 1-adamantylamine was added and the resulting mixture was heated at 60° C. with continuous stirring for a period of 16 hrs when TLC indicated the reaction was complete. The mixture was cooled to 0° C. and poured into water. The resulting yellow solid was collected and filtered to give the crude amide that was further purified by chromatography over silica gel using 50–90% ethyl acetate in hexane as eluent. Evaporation of the solvent yielded 600 mg of pure 7.

Workup

  1. temperatureTo an oven dried Argon cooled 100 mL flask
  2. temperaturethe resulting mixture was heated at 60° C.
  3. stirringwith continuous stirring for a period of 16 hrs when TLC
  4. temperatureThe mixture was cooled to 0° C.
  5. customThe resulting yellow solid was collected
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1e6c4a47b7924dd79ac61ef9e0d5faf7
Source dataset
uspto-grants-2008_05
Patent number
US07375118B2

Reaction notes

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