Dimethylamine → HCID 10159659, compound

HRID 861148Notes

Reaction equation

HRID 861148 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33].C(OCC)(=O)C>CN(C)C=O>[CH:18]1([NH:17][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)=[N:8][N:7]4[C:2]([N:32]([CH3:33])[CH3:31])=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[CH:15][N:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 10202263HCID 10202263, compound

Product 1

HCID 10159659HCID 10159659, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[7-chloro-2-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (60 mg, 0.14 mmol) in N,N-dimethylformamide (10 mL) was added dimethylamine (7 mL 40% in water). The solution was heated in a steal bomb at 100° C. for 3 days. The bomb was cooled to room temperature and ethyl acetate was added to the reaction mixture. The organics were washed with water, brine and dried over magnesium sulfate. Filtration and concentration followed by purification with flash chromatography (95:5-dichloromethane: methanol) gave 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)-N,N-dimethylpyrazolo[1,5-a]pyridin-7-amine (43 mg, 70%) as a yellow foam. 1H NMR (CDCl3) δ 8.11 (d, 1H), 7.95 (s, 1H), 7.35–7.30 (m, 2H), 7.24–7.21 (m, 2H), 6.97 (dd, 1H), 6.36 (d, 1H), 6.32 (d, 1H), 5.40 (broad s, 1H), 4.37 (m, 1H), 3.80 (s, 3H), 3.12 (s, 6H), 2.11–2.06 (m, 2H), 1.77–1.56 (m, 6H); MS m/z 429.

Workup

  1. temperatureThe bomb was cooled to room temperature
  2. washThe organics were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customfollowed by purification with flash chromatography (95:5-dichloromethane: methanol)

Sources & evidence

ORD record
ord-7c80929432a843278eddeda7ae73a433
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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