Hydrochloric Acid → N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine

HRID 861118Notes

Reaction equation

HRID 861118 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:26]3[CH:31]=[CH:30][C:29]([N:32]=C(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:28][CH:27]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].Cl.CCOCC.C(=O)(O)[O-].[Na+]>O1CCCC1>[NH2:32][C:29]1[CH:28]=[CH:27][C:26]([C:13]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:16]=3)=[C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:11]3[N:12]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 57444722HCID 57444722, compound

Product 1

HCID 10113479N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-butyl-3-[2-(butylamino)-4-pyrimidinyl]-2-{4-[(diphenylmethylene)-amino]phenyl}pyrazolo[1,5-a]pyridin-7-amine (1.0 g, 1.7 mmol) in tetrahydrofuran (50 mL) was added hydrochloric acid (10 mL, 4 N aqueous). The resultant solution was stirred at room temperature for 30 minutes. Ether was added and the solution was made basic by the slow addition of saturated aqueous sodium bicarbonate. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 hexanes:ethyl acetate) provided N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine as an orange oil. 1H NMR (CDCl3): δ 8.02 (d, 1 H), 7.81 (d, 1 H), 7.47 (d, 2 H), 7.31 (m, 1 H), 6.77 (d, 2 H), 6.42 (d, 1 H), 6.08 (m, 1 H), 6.00 (d, 1 H), 5.18 (broad, 1 H), 3.86 (broad, 2 H), 3.53 (m, 2 H), 3.39 (m, 2 H), 1.82–1.64 (m, 4 H), 1.58–1.46 (m, 4 H), 1.04–0.99 (m, 6 H); MS m/z430 (M+1). This material was treated with anhydrous hydrochloric acid in ether to provide the corresponding hydrochloride salt.

Workup

  1. washThe organic layer was washed with brine
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organics dried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-e63f88e91837491f958dd067bc6a3f23
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

Loading…