HCID 21923089, compound → HCID 178446121, compound

HRID 1272644Notes

Reaction equation

HRID 1272644 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>O.C(OCC)(=O)C>[ClH:1].[ClH:1].[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 21923089HCID 21923089, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178446121HCID 178446121, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The operation is carried out as in Stage 3 of Example 3 starting from 97 mg of the product obtained in Stage 1 above and 350 mg of trans-1,4-diaminocyclohexane and the reaction medium is taken to a temperature of 140 to 150° C. for approximately 4 hours then cooled down to 70–80° C. and diluted with 20 ml of water/ethyl acetate in a proportion of 50/50, left to settle, followed by washing with 10 ml of water and 5 ml of an aqueous solution of sodium chloride, drying and evaporating to dryness. After purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 and salification with 1.4 N hydrochloric acid in ethanol, 66 mg of expected product is obtained in the form of crystals.

Workup

  1. temperaturethen cooled down to 70–80° C.
  2. waitleft
  3. washby washing with 10 ml of water and 5 ml of an aqueous solution of sodium chloride
  4. customdrying
  5. customevaporating to dryness
  6. customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 and salification with 1.4 N hydrochloric acid in ethanol

Sources & evidence

ORD record
ord-77dc97271e3341969bc28c66f7fe09f4
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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