Morpholine → HCID 10298898, compound

HRID 861154Notes

Reaction equation

HRID 861154 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.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[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]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[CH:15][N:14]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 57444748HCID 57444748, compound

Product 1

HCID 10298898HCID 10298898, compoundYield 86%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (75 mg, 0.18 mmol) and morpholine (5 mL, 57 mmol) was heated at 120° C. for 4 hours, then cooled and concentrated. Flash chromatography (3:1 to 1:3 hexanes-ethyl acetate) afforded N-cyclopentyl-4-[2-(4-methoxyphenyl)-7-(4-morpholinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (72 mg, 86%) as a yellow solid. 1H NMR (CDCl3): δ 8.14 (d, 1 H), 7.93 (broad, 1 H), 7.58 (d, 2 H), 7.33 (t, 1 H), 6.97 (d, 2 H), 6.35 (m, 2 H), 4.38 (m, 1 H), 3.99 (m, 4 H), 3.87 (s, 3 H), 3.50 (m, 4 H), 2.08 (m, 2 H), 1.79–1.54 (m, 6 H); MS m/z 471 (M+1).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8564cd68e0fa4a5ba91f74f07e3360e8
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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