Hydrochloric Acid → 2-[2-(5-Aminopyridin-3-yl)ethyl]-N(4)-(2,5-dichloropyrimidin-4-yl)benzene-1,4-diamine Trihydrochloride

HRID 541756Notes

Reaction equation

HRID 541756 reaction equation
[ClH:1].O1CCOCC1.C(OC([NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:28]([Cl:29])=[CH:27][N:26]=[C:25]([Cl:30])[N:24]=2)=[CH:18][C:17]=1[CH2:31][CH2:32][C:33]1[CH:34]=[C:35]([NH:39]C(=O)OC(C)(C)C)[CH:36]=[N:37][CH:38]=1)=O)(C)(C)C>CO>[ClH:29].[ClH:1].[ClH:29].[NH2:39][C:35]1[CH:34]=[C:33]([CH2:32][CH2:31][C:17]2[CH:18]=[C:19]([NH:22][C:23]3[C:28]([Cl:29])=[CH:27][N:26]=[C:25]([Cl:30])[N:24]=3)[CH:20]=[CH:21][C:16]=2[NH2:15])[CH:38]=[N:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57962746tert-Butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

Product 1

HCID 866362512-[2-(5-Aminopyridin-3-yl)ethyl]-N(4)-(2,5-dichloropyrimidin-4-yl)benzene-1,4-diamine TrihydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.0 M of hydrogen chloride in 1,4-dioxane (30 mL, 120 mmol), tert-butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate (860 mg, 1.49 mmol) and methanol (15 mL) was stirred at 25° C. for 1 hour. The solvent was removed in vacuo. The crude residue was dissolved in DCM and triturated with ether to give the desired product (0.57 g, 73%). LCMS calculated for C17H17Cl2N6(M+H)+: m/z=375.0, 377.0.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe crude residue was dissolved in DCM
  3. customtriturated with ether

Sources & evidence

ORD record
ord-9cfbc3a797ba413d94f5a47016795a78
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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