Dimethylamine → HCID 10161966, compound

HRID 1373819Notes

Reaction equation

HRID 1373819 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH2:17]I)[N:14]=[C:13]([NH:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:32][NH:33][CH3:34]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH2:17][N:33]([CH3:34])[CH3:32])[N:14]=[C:13]([NH:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 87838342HCID 87838342, compound

Product 1

HCID 10161966HCID 10161966, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-(iodomethyl)-2-pyrimidinamine (160 mg, 0.29 mmol) in tetrahydrofuran (2 mL) was added dimethylamine (730 μL, 2 M in THF, 1.5 mmol) and the reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water, and brine. The organic layer was dried over magnesium sulfate. Filtration and concentration provided the crude amine (120 mg, 88%). A portion of the crude amine (26 mg) was purified by flash chromatography (38:2 dichloromethane:methanol to 37:3 dichloromethane-methanol) to provide 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-[(dimethylamino)methyl]-2-pyrimidinamine (15 mg). Rf 0.32 (37:3 dichloromethane:methanol); 1H NMR (CDCl3) δ 8.37 (d, 1H), 7.66 (m, 2H), 7.26 (m, 1H), 7.11 (t, 2H), 7.03 (d, 1H), 6.39 (s, 1H), 5.18 (d, 1H), 4.35 (m, 1H), 3.23 (s, 2H), 2.22 (s, 6H), 2.07 (m, 2H), 1.80–1.45 (m, 6H); MS m/z 465 (M+1); mp 68–75° C.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution, water, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customprovided the crude amine (120 mg, 88%)
  5. customA portion of the crude amine (26 mg) was purified by flash chromatography (38:2 dichloromethane:methanol to 37:3 dichloromethane-methanol)

Sources & evidence

ORD record
ord-d06b8337262f4084881c9b5e9699e0c1
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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