Trifluoroacetic acid → 6-(cis-2-Aminocyclohexylamino)-5-chloro-2-(5-methylpyridin-3-ylamino)nicotinamide.hydrochloride

HRID 1620123Notes

Reaction equation

HRID 1620123 reaction equation
[Cl:1][C:2]1[C:3]([NH:28][C@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[NH:35]C(=O)OC(C)(C)C)=[N:4][C:5]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=2)=[C:6]([C:8]([NH:10]C(C2C=CC=CC=2)(C)C)=[O:9])[CH:7]=1.C(O)(C(F)(F)F)=O>>[NH2:35][C@H:30]1[CH2:31][CH2:32][CH2:33][CH2:34][C@H:29]1[NH:28][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[C:5]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=2)[N:4]=1.[ClH:1]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683894HCID 86683894, compound

Product 1

HCID 867625046-(cis-2-Aminocyclohexylamino)-5-chloro-2-(5-methylpyridin-3-ylamino)nicotinamide.hydrochlorideYield 192.3%

Procedure

A mixture of tert-butyl cis-2-(3-chloro-5-(2-phenylpropan-2-ylaminocarbonyl)-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate (12 mg) and TFA (0.5 ml) was stirred at room temperature for 1 hour. The solvent was distilled away under reduced pressure (at 40° C. or less), ethyl acetate and 4N hydrogen chloride/1,4-dioxane (25 μl) were added, and the resultant was left at rest overnight at room temperature. Solid matter was collected by filtration, and a white solid of 6-(cis-2-aminocyclohexylamino)-5-chloro-2-(5-methylpyridin-3-ylamino)nicotinamide•hydrochloride (8 mg) was thus obtained.

Workup

  1. distillationThe solvent was distilled away under reduced pressure (at 40° C. or less), ethyl acetate and 4N hydrogen chloride/1,4-dioxane (25 μl)
  2. additionwere added
  3. waitthe resultant was left at rest overnight at room temperature
  4. filtrationSolid matter was collected by filtration

Sources & evidence

ORD record
ord-d39c5c2ad9c14d0098c0e3e882beb1c4
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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