Dichloromethane → N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-4-methoxy-benzamide

HRID 1244953Notes

Reaction equation

HRID 1244953 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(Cl)Cl.C(N(CC)CC)C.[C:30](Cl)(=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1>O>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:30](=[O:39])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21923060N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-4-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

280 mg of the product obtained in Stage 1 of Example 7, 4 ml of methylene chloride, 0.28 ml triethylamine and 0.18 ml of 4-anisoyl chloride are mixed together then the reaction medium is agitated at ambient temperature for 30 minutes. Then 2 ml of water is added, followed by extracting with methylene chloride, drying and evaporating the solvents. Chromatography on silica is carried out (eluent methylene chloride/methanol/ammonium hydroxide 85/15/1.5 then CH2Cl2/CH3CN 8/2 then methylene chloride/methanol/ammonium hydroxide 85/15/1.5). 275 mg of expected product is collected.

Workup

  1. extractionby extracting with methylene chloride
  2. customdrying
  3. customevaporating the solvents
  4. custom275 mg of expected product is collected

Sources & evidence

ORD record
ord-803d2c5a46404336b2b713d5d354e49d
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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