Benzenemethanamine, 3-chloro- → HCID 178483760, compound

HRID 1809780Notes

Reaction equation

HRID 1809780 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][C:16]([NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[N:17][CH:18]=3)[NH:13][N:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31]>>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH:31][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][C:16]([NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[N:17][CH:18]=3)[NH:13][N:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 178483761HCID 178483761, compound

Product 1

HCID 178483760HCID 178483760, compound

Conditions

Temperature
130 °C

Procedure

The mixture of N′-[3-(2-methanesulfonyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-N,N-dimethyl-ethane-1,2-diamine (from Example 23 supra) (160 mg, crude) and 3-chlorobenzylamine (236 mg, 1.67 mmol) was heated at 130° C. with stirring for 3 hours. The resulting oil was purified by chromatography (silica gel, 7 g, 200-300 mesh, eluting with dichloromethane:methanol, 10:1) and further purified by prep-HPLC. Concentrated HCl was added to the fractions with product and concentrated under reduced pressure to give N-{3-[2-(3-chloro-benzylamino)-pyrimidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-N′,N′-dimethyl-ethane-1,2-diamine; hydrochloride. (Yield 26 mg).

Workup

  1. customThe resulting oil was purified by chromatography (silica gel, 7 g, 200-300 mesh, eluting with dichloromethane:methanol, 10:1)
  2. customfurther purified by prep-HPLC
  3. additionConcentrated HCl was added to the fractions with product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa6970ae601c48a3813c08235709f5ba
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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