Morpholine → HCID 10140929, compound

HRID 456703Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 10274600HCID 10274600, compound

Product 1

HCID 10140929HCID 10140929, compoundYield 6%

Conditions

Temperature: 150 °C

Procedure

A thick walled glass tube was charged with N-{4-[8-chloro-2-(3-nitrophenyl)imidazo[1,2-α]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (44 mg, 0.10 mmol) and morpholine (4 mL). The vessel was sealed and heated to 150° C. for 4 days. The mixture was concentrated in vacuo and purified via flash chromatography on silica gel (2:1 to 1:1 hexanes:ethyl acetate) to provide N-cyclopentyl-4-[8-(4-morpholinyl)-2-(3-nitrophenyl)imidazo[1,2-α]pyridin-3-yl]-2-pyrimidinamine (3 mg, 6%) as a yellow solid. 1H NMR (CDCl3): δ 8.92 (m, 1H), 8.67 (s, 1H), 8.21 (d, 1H), 8.13 (m, 1H), 8.01 (d, 1H), 7.53 (t, 1H), 6.83 (t, 1H), 6.61 (d, 1H), 6.40 (d, 1H), 5.33 (m, 1H), 4.33 (m, 1H), 4.00 (m, 4H), 3.58 (m, 4H), 2.14–2.06 (m, 2H), 1.83–1.54 (m, 6H); MS m/z 486 (M+1).

Workup

customThe vessel was sealed
concentrationThe mixture was concentrated in vacuo
custompurified via flash chromatography on silica gel (2:1 to 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-7913c7e459e54962a24f2392db9037f4
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186714B2

Reaction notes

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