Acetic Acid → HCID 10118434, compound

HRID 861119Notes

Reaction equation

HRID 861119 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:23]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:33]1(=O)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.CCOCC>[CH2:17]([NH:16][C:15]1[N:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:7][CH:6]=3)[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:23]=3)=[C:11]2[CH:12]=[CH:13][CH:14]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10113479N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine

Product 1

HCID 10118434HCID 10118434, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine (62 mg, 0.15 mmol) in 1,2-dichloroethane (2 mL) was treated with cyclohexanone (0.02 mL, 0.22 mmol), acetic acid (0.04 mL, 0.72 mmol), and sodium triacetoxyborohydride (61 mg, 0.29 mmol). The resultant solution was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate was added dropwise followed by ether. 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 (4:1 to 2:1 hexanes-ethyl acetate) provided N-butyl-3-[2-(butylamino)-4-pyrimidinyl]-2-[4-(cyclohexylamino)phenyl]pyrazolo[1,5-a]pyridin-7-amine (54 mg, 73%) as an orange oil. 1H NMR (CDCl3): δ 7.94 (d, 1 H), 7.73 (d, 1 H), 7.39 (d, 2 H), 7.23 (m, 1 H), 6.59 (d, 2 H), 6.41 (d, 1 H), 6.03 (m, 1 H), 5.91 (d, 1 H), 5.11 (broad, 1 H), 3.66 (broad, 1 H), 3.44 (m, 2 H), 3.30 (m, 3 H), 2.05 (m, 2 H), 1.75–1.12 (m, 16 H), 0.95–0.92 (m, 6 H); MS m/z 512 (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-e03304976db242a7836b0d8841e70fac
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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