Hydrochloric Acid → HCID 136336332, compound

HRID 2218255Notes

Reaction equation

HRID 2218255 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:25]([CH3:27])[CH3:26])=[C:14]([NH:16][C:17](=[O:24])[CH2:18][NH:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:15]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34]CC2C=CC(OC)=CC=2)[N:3]=1.FC(F)(F)C(O)=O.[ClH:51]>C1(OC)C=CC=CC=1.O.C1(C)C=CC=CC=1.O1CCOCC1>[ClH:51].[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:25]([CH3:27])[CH3:26])=[C:14]([NH:16][C:17](=[O:24])[CH2:18][NH:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:15]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[N:3]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69145292HCID 69145292, compound

Product 1

HCID 136336332HCID 136336332, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 7519AnisoleSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N1-[5-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)-2-(dimethylamino)-phenyl]-N2-(cyclopropylmethyl)glycinamide (0.130 g, 0.448 mmol) in anisole (1 mL) and water (1 mL) was added trifluoroacetic acid (5 mL). The mixture was stirred at room temperature for 20 hrs. The reaction mixture was diluted with toluene and concentrated under reduced pressure. The residue was suspended in hexane and the precipitate was collected by filtration. The solid obtained was dissolved in TB and 4N HCl in 1,4-dioxane was added to the solution. The resulting solid was collected by filtration, washed with THF and 1,4-dioxane, and dried under reduced pressure to give N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(dimethylamino)phenyl]-N2-(cyclopropylmethyl)glycinamide hydrochloride as a yellow solid (0.085 g, yield 77%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationthe precipitate was collected by filtration
  3. customThe solid obtained
  4. additionwas added to the solution
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with THF and 1,4-dioxane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3675720895fe4bcb94db765b3daaedc5
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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