1,2-Diaminocyclohexane, trans- → (trans)-N1-(6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)cyclohexane-1,2-diamine

HRID 2089010Notes

Reaction equation

HRID 2089010 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([Cl:17])[N:3]=1.[C@@H:18]1([NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[NH2:24]>C(#N)C>[Cl:17][C:4]1[N:3]=[C:2]([NH:24][C@@H:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]2[NH2:25])[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 438061,2-Diaminocyclohexane, trans-HCID 87191335CID 87191335

Product 1

HCID 89534428(trans)-N1-(6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)cyclohexane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 61a (3.4 g) in acetonitrile (30 mL) and trans-cyclohexane-1,2-diamine was heated at 170° C. for 40 minutes in a Biotage microwave reactor. The reaction mixture was extracted with ethyl acetate (2×), washed with brine and sodium bicarbonate. The combined organic layers were treated with 1M HCl. The aqueous layer was treated with NaOH (1M) and the material crashed out of the solution to give 0.797 mg of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×)
  2. washwashed with brine and sodium bicarbonate
  3. additionThe combined organic layers were treated with 1M HCl
  4. additionThe aqueous layer was treated with NaOH (1M)

Sources & evidence

ORD record
ord-c11140dc5b994942ba2ad213211afda9
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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