Cesium carbonate → HCID 22732293, compound

HRID 1357727Notes

Reaction equation

HRID 1357727 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[C:17]([NH:19][C:20]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH:23]=4)=[O:21])[CH:16]=[CH:15][C:14]=3[CH3:34])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:35][CH3:36].C1(C)C=CC(S(O[CH2:47][CH2:48][N:49]2[CH:53]=[CH:52][N:51]=[N:50]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH3:36][O:35][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:47][CH2:48][N:49]1[CH:53]=[CH:52][N:51]=[N:50]1)[N:9]=[CH:8][N:7]=[C:6]2[NH:12][C:13]1[CH:18]=[C:17]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:23]=2)=[O:21])[CH:16]=[CH:15][C:14]=1[CH3:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonateHCID 136116301HCID 136116301, compound

Product 1

HCID 22732293HCID 22732293, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-hydroxy-6-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline (184 mg), 2-(1,2,3-triazol-1-yl)ethyl 4-toluenesulphonate (101 mg), cesium carbonate (370 mg) and N,N-dimethylacetamide (4 ml) was stirred and heated to 100° C. for 1 hour. After cooling the reaction mixture to ambient temperature, the reaction mixture was partitioned between water and methylene chloride. The organic phase was dried with brine and sodium sulphate and evaporated. The material so obtained was purified by column chromatography on silica using a 10:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (47 mg); NMR: 2.14 (s, 3H), 3.51 (t, 4H), 3.72 (t, 4H), 3.91 (s, 3H), 4.59 (t, 2H), 4.87 (t, 2H), 7.09 (d, 1H), 7.2 (s, 1H), 7.22 (d, 1H), 7.27 (d, 1H), 7.58 (m, 1H), 7.74 (s, 2H), 7.83 (s, 1H), 8.18 (s, 1H), 8.24 (d, 1H), 8.26 (s, 1H), 9.39 (s, 1H), 10.28 (s, 1H); m/s: M+H+ 582.

Workup

  1. temperatureAfter cooling the reaction mixture to ambient temperature
  2. customthe reaction mixture was partitioned between water and methylene chloride
  3. dry with materialThe organic phase was dried with brine and sodium sulphate
  4. customevaporated
  5. customThe material so obtained
  6. customwas purified by column chromatography on silica using
  7. additiona 10:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-598f40433ec341aaa29e277afc366256
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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