Morpholine → HCID 10225376, compound

HRID 861156Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 86596768HCID 86596768, compound

Product 1

HCID 10225376HCID 10225376, compoundYield 93.2%

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopropyl-2-pyrimidinamine (75 mg, 0.19 mmol) and morpholine (2 mL, 23 mmol) was heated in a sealed tube at 140° C. for 4 hours. After cooling to room temperature, the mixture was concentrated. Flash chromatography (1:1 to 1:3 hexanes-ethyl acetate) provided N-cyclopropyl-4-[2-(4-methoxyphenyl)-7-(4-morpholinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (78.4 mg, 92%) as an off-white solid. 1H NMR (CDCl3): δ 8.29 (d, 1 H), 8.08 (d, 1 H), 7.61 (d, 2 H), 7.31 (t, 1 H), 6.98 (d, 2 H), 6.45 (d, 1 H), 6.33 (d, 1 H), 5.40 (broad, 1 H), 4.00 (m, 4 H), 3.89 (d, 3 H), 3.51 (m, 4 H), 2.88 (m, 1 H), 0.89 (m, 2 H), 0.65 (m, 2 H); MS m/z 443 (M+1).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-027231fb8c52495b9691a998461345f0
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153855B2

Reaction notes

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