HCID 21923035, compound → HCID 178478595, compound

HRID 1272630Notes

Reaction equation

HRID 1272630 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][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:3]=1.[NH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31][CH2:30]1>O>[ClH:1].[ClH:1].[ClH:1].[NH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH:35][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][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[N:3]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 21923035HCID 21923035, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478595HCID 178478595, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The operation is carried out as in Stage 3 of Example 7 starting from 242 mg of the product obtained in Stage 1 above and 680 mg of trans-1,4-diaminocyclohexane and the reaction medium is heated to approximately 140° C. for approximately 3 hours 30 minutes, then poured into H2O, followed by extracting with 3×10 ml of ethyl acetate and washing with 10 ml of saturated sodium chloride. After purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/15/1.5, salification is carried out with HCl/EtOH 1.4N, followed by filtering, washing with 5 ml EtOH then drying at ˜50° C.

Workup

  1. extractionby extracting with 3×10 ml of ethyl acetate
  2. washwashing with 10 ml of saturated sodium chloride
  3. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/15/1.5, salification
  4. filtrationby filtering
  5. washwashing with 5 ml EtOH
  6. customthen drying at ˜50° C.

Sources & evidence

ORD record
ord-330858a26fb84959b578fa528700e720
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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