Ethyl Acetate → HCID 178492896, compound

HRID 1244935Notes

Reaction equation

HRID 1244935 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[N:3]=1.[NH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([NH2:38])[CH2:34][CH2:33]1.CCOC(C)=O>O>[ClH:1].[ClH:1].[NH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([NH:38][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[N:3]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21923051N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-4-methoxy-benzenesulphonamideHCID 178511674HCID 178511674, compound

Product 1

HCID 178492896HCID 178492896, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The operation is carried out as in Stage 2 of Example 10 starting from 126 mg of the product obtained in Stage 1 above and 319 mg of trans-1,4-diaminocyclohexane and the reaction medium is heated to approximately 140° C. for approximately 3 hours, left to return to 80° C., 5 ml of AcOEt is added, 5 ml of warm water is 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 95 mg of expected product is obtained in the form of a beige solid.

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-e2b6bbac500b4957b896a97690e6a592
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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