Diethyl Ether → HCID 10117059, compound

HRID 1796542Notes

Reaction equation

HRID 1796542 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][C:8]=2[C:35](OCC)=[O:36])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.CCOCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][C:8]=2[CH2:35][OH:36])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 10279971HCID 10279971, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10117059HCID 10117059, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of ethyl 7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylate (50 mg, 0.095 mmol) in dichloromethane (1 mL) was added diisobutylaluminum hydride (490 μL, 1.0 M in hexanes, 0.49 mmol). The reaction mixture was stirred at −78° C. for 2 hours then poured into a stirring mixture of ether and aqueous Rochelle's salt (sodium potassium tartrate) solution. The resultant mixture was stirred at room temperature for 16 hours. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine. Concentration followed by flash chromatography on silica (29:1 dichloromethane:methanol) provided [7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo-[1,5-a]pyridin-6-yl]methanol (27 mg, 59%) as a green solid. Rf0.26 (29:1 dichloromethane:methanol); 1H NMR (300 MHz, CDCl3): δ 7.99 (d, 1H), 7.70 (d, 1H), 7.61 (m, 2H), 7.23 (d, 1H), 7.13 (t, 2H), 6.29–6.24 (m, 2H), 5.08 (d, 1H), 4.79 (s, 2H), 4.47 (broad, 1H), 4.29 (m, 1H). 2.09–1.99 (m, 4H), 1.85–1.48 (m, 12H); MS m/z 487 (M+1).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. concentrationConcentration

Sources & evidence

ORD record
ord-39865516bfea461ead5ff183794dafe6
Source dataset
uspto-grants-2006_04
Patent number
US07030134B2

Reaction notes

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