Dichloromethane → HCID 21922904, compound

HRID 1244923Notes

Reaction equation

HRID 1244923 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.[CH2:23](N(CC)CC)C.Cl[S:31]([C:34]1[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37])(=[O:33])=[O:32]>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][S:31]([C:34]2[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=2[C:36]([O:38][CH2:39][CH3:23])=[O:37])(=[O:33])=[O:32])[N:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21922904HCID 21922904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The operation is carried out as in Stage 1 of Example 10 starting from 280 mg of the product obtained in Stage 1 of Example 7, 4 ml of methylene chloride, 0.2 ml of triethylamine and 400 mg of methyl 2-(chlorosulphonyl)benzoate in place of 4-methyl-benzenesulphonic acid chloride then the reaction medium is agitated at ambient temperature for approximately 30 minutes. Then 5 ml of water is added, followed by extracting with 2×10 ml of methylene chloride, washing with 5 ml of H2O, drying and evaporating. After chromatography on silica eluting with methylene chloride/ethyl acetate in a proportion of 70/30, 129 mg of expected product is thus obtained.

Workup

  1. extractionby extracting with 2×10 ml of methylene chloride
  2. washwashing with 5 ml of H2O
  3. customdrying
  4. customevaporating

Sources & evidence

ORD record
ord-19d56121aeba45e1a3d2fdb0fae97167
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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