Ethyl Acetate → HCID 178478743, compound

HRID 1244937Notes

Reaction equation

HRID 1244937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][NH:14][C:15]2[N:23]=[C:22](Cl)[N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]1.CCOC(C)=O>O>[ClH:1].[ClH:1].[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:22]2[N:21]=[C:20]3[C:16]([N:17]=[CH:18][N:19]3[CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:15]([NH:14][CH2:13][CH2:12][NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])[N:23]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 219229724-chloro-N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-benzenesulphonamideHCID 178511674HCID 178511674, compound

Product 1

HCID 178478743HCID 178478743, compoundYield 158.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The operation is carried out as in Stage 2 of Example 10 starting from 161 mg of the product obtained in Stage 1 above and 403 mg of trans-1,4-diaminocyclohexane and the reaction medium is heated to approximately 140° C. for approximately 3 hours 30 minutes left to return to 80° C., 5 ml of AcOEt then 5 ml of warm water are added, the reaction medium is left to return to ambient temperature, followed by extracting with 2×5 ml of ethyl acetate, washing with 5 ml of saturated sodium chloride, then drying. After purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/15/1.5, 5 ml of 1.4N hydrochloric acid/ethanol is added, the reaction medium is left to crystallize, followed by filtering, rinsing with 5 ml of ether and drying under vacuum. In this way 113 mg of expected product is obtained in the form of beige white crystals.

Workup

  1. waitleft
  2. customto return to 80° C.
  3. waitthe reaction medium is left
  4. customto return to ambient temperature
  5. extractionby extracting with 2×5 ml of ethyl acetate
  6. washwashing with 5 ml of saturated sodium chloride
  7. customdrying
  8. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/15/1.5, 5 ml of 1.4N hydrochloric acid/ethanol
  9. additionis added
  10. waitthe reaction medium is left
  11. customto crystallize
  12. filtrationby filtering
  13. washrinsing with 5 ml of ether
  14. customdrying under vacuum

Sources & evidence

ORD record
ord-c88672fb83344fcebd500ab1b3e1e76d
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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