Morpholine → HCID 10143725, compound

HRID 456708Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 10165406HCID 10165406, compound

Product 1

HCID 10143725HCID 10143725, compoundYield 24%

Procedure

In a similar manner as described in Example 3 from N-cyclopentyl-4-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-2-pyrimidinamine (100 mg, 0.19 mmol) and morpholine at 100° C. for 3 days was obtained N-cyclopentyl-4-[2-(4-fluorophenyl)-6,8-di(4-morpholinyl)imidazo[1,2-a]pyridin-3-yl]-2-pyrimidinamine (25 mg, 24%) as a yellowish solid. 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.11 (d, 1H), 7.66 (q, 2H), 7.10 (t, 2H), 6.49 (d, 1H), 6.43 (d, 1H), 5.24 (d, 1H), 4.45 (m, 1H), 4.03 (m, 4H), 3.94 (m, 4H), 3.60 (m, 4H), 3.13 (m, 4H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); 19F NMR (CDCl3) δ −114.1; MS m/z 545 (M+1).

Sources & evidence

ORD record: ord-08a74d521c594917bec19a3d248de3f9
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186714B2

Reaction notes

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