2-Morpholinoethylamine → HCID 10229480, compound

HRID 861152Notes

Reaction equation

HRID 861152 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][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.[NH2:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C>[CH:18]1([NH:17][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[N:8][N:7]4[C:2]([NH:31][CH2:32][CH2:33][N:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[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 4082852-MorpholinoethylamineHCID 21226206Ethyl acetate hexaneHCID 57444748HCID 57444748, compound

Product 1

HCID 10229480HCID 10229480, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (150 mg, 0.36 mmol) and 4-(2-aminoethyl)morpholine (3 mL, 21.2 mmol) was heated at 140° C. for 4 hours. Concentration of the reaction mixture followed by flash chromatography (3:1 ethyl acetate-hexane to ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-methoxyphenyl)-N-[2-(4-morpholinyl)ethyl]pyrazolo[1,5-a]pyridin-7-amine (135 mg, 74%) as a pale yellow foam. 1H NMR (CDCl3): δ 8.01 (d, 1 H), 7.78 (d, 1 H), 7.61 (d, 2 H), 7.30 (t, 1 H), 6.99 (d, 2 H), 6.52 (t, 1 H), 6.36 (d, 1 H), 5.98 (d, 1 H), 5.08 (d, 1 H), 4.37 (m, 1 H), 3.88 (s, 3 H), 3.76 (m, 4 H), 3.46 (q, 2 H), 2.76 (t, 2 H), 2.54 (m, 4 H), 2.12–1.52 (m, 8 H); MS m/z 514 (M+1).

Sources & evidence

ORD record
ord-b8678a0368fa4c609e8b035969e986d2
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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