HCID 21922986, compound → HCID 11365078, compound

HRID 1272637Notes

Reaction equation

HRID 1272637 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][S:13][CH2:12]2)=[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>>[ClH:1].[ClH:1].[NH2:28][CH:29]1[CH2:34][CH2:33][CH: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][S:13][CH2:12]3)=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:3]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 21922986HCID 21922986, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 11365078HCID 11365078, compoundYield 92.3%

Procedure

The operation is carried out as in Stage 3 of Example 5 starting from 186 mg of the product obtained in Stage 1 above and 513 mg of trans-1,4-diaminocyclohexane, the reaction medium is taken to a temperature of approximately 140 to 145° C. for 4 hours 30 minutes then left to return to ambient temperature. 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, separation is carried out, followed by washing with 10 ml of ethanol and drying at a temperature of approximately 50° C. In this way 117 mg of expected product is obtained in the form of pink beige crystals.

Workup

  1. waitthen left
  2. customto return to ambient temperature
  3. customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 and salification
  4. customwith 1.4 N hydrochloric acid in ethanol, separation
  5. washby washing with 10 ml of ethanol
  6. customdrying at a temperature of approximately 50° C

Sources & evidence

ORD record
ord-8750822a3f8a43ee83b316ed6822f5b1
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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