HCID 178478377, compound → HCID 178479269, compound

HRID 1453559

Reaction equation

HRID 1453559 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][NH:16]2)=[C:12]([N:19]2[C:23]3[CH:24]=[C:25]([Cl:29])[C:26]([Cl:28])=[CH:27][C:22]=3[N:21]=[CH:20]2)[N:11]=1>>[ClH:9].[Cl:28][C:26]1[C:25]([Cl:29])=[CH:24][C:23]2[N:19]([C:12]3[N:11]=[C:10]([NH:1][C@H:2]4[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]4)[N:18]=[C:17]4[C:13]=3[N:14]=[CH:15][NH:16]4)[CH:20]=[N:21][C:22]=2[CH:27]=1

Participants

3

Reactant 2

HCID 178478377HCID 178478377, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178479269HCID 178479269, compoundYield 15%

Conditions

Temperature
110 °C

Procedure

570 mg of trans-1,4-diaminocyclohexane are brought to its melting temperature (70° C.), 170 mg of product obtained in stage 1 above are added in a single step, and the mixture is then heated at 110° C. for approximately 24 hours. The mixture is allowed to return to ambient temperature. Purification is carried out by chromatography on silica with an MeOH—NH4OH: 98-2 mixture for eluent. The purified product is dissolved in ethanol and HCl-AcOEt (hydrochloric acid-ethyl acetate) is then added. Partial drying and drying under vacuum at 50° C. are carried out. 34 mg of expected product are obtained in the form of brown-colored crystals.

Workup

  1. additionabove are added in a single step
  2. customto return to ambient temperature
  3. customPurification
  4. dissolutionThe purified product is dissolved in ethanol
  5. additionHCl-AcOEt (hydrochloric acid-ethyl acetate) is then added
  6. customPartial drying
  7. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-0a5788f00ccd4af491e7205b67062579
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Linked notes

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