HCID 21923081, compound → HCID 178478744, compound

HRID 1272651Notes

Reaction equation

HRID 1272651 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]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[N:3]=1.[NH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]1>O>[ClH:1].[ClH:1].[NH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[N:3]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 21923081HCID 21923081, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478744HCID 178478744, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The operation is carried out as in Stage 2 of Example 10 starting from 292 mg of the product obtained in Stage 1 above and 810 mg of trans-1,4-diaminocyclohexane and the reaction medium is heated to approximately 140° C. for approximately 3 hours then returned to 80° C., 5 ml of AtOEt then 10 ml of warm water are added, followed by leaving to return to ambient temperature, extracting with 2×10 ml of ethyl acetate, washing with 10 ml of saturated sodium chloride and 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 167 mg of expected product is obtained in the form of white solid.

Workup

  1. customthen returned to 80° C.
  2. customby leaving
  3. customto return to ambient temperature
  4. extractionextracting with 2×10 ml of ethyl acetate
  5. washwashing with 10 ml of saturated sodium chloride
  6. customdrying
  7. 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
  8. additionis added
  9. waitthe reaction medium is left
  10. customto crystallize
  11. filtrationby filtering
  12. washrinsing with 5 ml of ether
  13. customdrying under vacuum

Sources & evidence

ORD record
ord-362ab32287e24fe8a92e9935660356c9
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

Loading…