Benzenemethanamine, 3-chloro- → HCID 178521287, compound

HRID 1809785Notes

Reaction equation

HRID 1809785 reaction equation
CS([C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][C:15]([NH:19][CH2:20][CH2:21][OH:22])=[N:16][CH:17]=3)[NH:12][N:11]=2)[CH:7]=[CH:6][N:5]=1)=O.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][NH2:28]>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][NH:28][C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][C:15]([NH:19][CH2:20][CH2:21][OH:22])=[N:16][CH:17]=3)[NH:12][N:11]=2)[CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 178504621HCID 178504621, compound

Product 1

HCID 178521287HCID 178521287, compound

Conditions

Temperature
130 °C

Procedure

The mixture of 2-[3-(2-methane sulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethanol (from Example 21 supra) (1.9 g, crude, 2.31 mmol) and 3-chlorobenzylamine (797 mg, 4.62 mmol) was heated at 130° C. with stirring for 3 hours. The solvent was removed under reduced pressure and the solid was purified by prep-TLC and prep-HPLC. Concentrated HCl was added to the fractions with product and concentrated under reduced pressure to give 2-{3-[2-(3-chloro-benzylamino)-pyrimidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino}-ethanol; hydrochloride. (Yield 28 mg, 3.1% of the 3 steps).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was purified by prep-TLC and prep-HPLC
  3. additionConcentrated HCl was added to the fractions with product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7668f7d69a043e188c368d66f54e1d9
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

Loading…