Bis-(1H-imidazol-2-YL)-methanone → HCID 11511363, compound

HRID 550496Notes

Reaction equation

HRID 550496 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][OH:32])[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:33](C1NC=CN=1)(C1NC=CN=1)=[O:34]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28][N:29]4[CH2:30][CH2:31][O:32][C:33]4=[O:34])[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 11532615HCID 11532615, compound

Product 1

HCID 11511363HCID 11511363, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-({2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}amino)ethanol (prepared as described in Example 36/27 mg, 0.06 mmol) was dissolved in DMA (0.7 ml) and carbonyl diimidazole (14 mg, 0.09 mmol) was added at −15° C. The temperature was slowly raised to room temperature and the reaction mixture was stirred for 1 hour. The crude mixture was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm) eluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient) to give the title compound (20 mg, 69%); NMR Spectrum: 3.67-3.71 (m, 4H), 4.29 (t, 2H), 4.44 (t, 2H), 5.28 (s, 2H), 7.24 (d, 1H), 7.37 (t, 1H), 7.58 (d, 1H), 7.74 (dd, 1H), 7.88 (t, 2H), 8.11 (d, 1H), 8.13 (s, 1H), 8.33 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 482 (MH+).

Workup

  1. customThe crude mixture was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm)
  2. washeluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient)

Sources & evidence

ORD record
ord-38018a54d08f42659406b3afa50b8014
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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