HCID 21923091, compound → HCID 178446122, compound

HRID 1272647Notes

Reaction equation

HRID 1272647 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][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=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.C(OCC)(=O)C>[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]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:4]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=3)[N:3]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 21923091HCID 21923091, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178446122HCID 178446122, compoundYield 135.3%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The operation is carried out as in Stage 3 of Example 3 starting from 160 mg of the product obtained in Stage 1 above and 456 mg of trans-1,4-diaminocyclohexane and the reaction medium is taken to a temperature of 140 to 150° C. for 4 hours then cooled down to 70–80° C. and diluted with 20 ml of water/ethyl acetate in a proportion of 50/50 and 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, 149 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-903f2070358f4e88b89b7d9233893ca9
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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