Cesium fluoride → HCID 69309204, compound

HRID 2117747Notes

Reaction equation

HRID 2117747 reaction equation
[F-].[Cs+].[CH2:3]([C:7]1[N:8]([CH2:41][CH2:42][CH3:43])[C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25](=[O:40])(=[O:39])[N:26]([CH2:35][CH2:36][O:37][CH3:38])COCC[Si](C)(C)C)=[CH:21][CH:20]=3)[N:13]=2)=[CH:10][N:11]=1)[CH2:4][CH:5]=[CH2:6]>CN(C=O)C.O>[CH2:3]([C:7]1[N:8]([CH2:41][CH2:42][CH3:43])[C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([S:25](=[O:40])(=[O:39])[NH:26][CH2:35][CH2:36][O:37][CH3:38])=[CH:23][CH:24]=3)[N:13]=2)=[CH:10][N:11]=1)[CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 69314279HCID 69314279, compound

Product 1

HCID 69309204HCID 69309204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of caesium fluoride (180 mg, 1.2 mmole), and 4-(2-(but-3-enyl)-1-propylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)-N-(2-trimethylsilylethoxymethyl)sulphamoyl]anilino}pyrimidine (Method 100; 100 mg, 0.17 mmol), in DMF (3 ml), was heated at 140° C. under nitrogen for 24 hours. The mixture was diluted with water and extracted with EtOAc. The extracts were washed with water and brine, dried, and the solvent evaporated. The residue was purified by chromatography on silica gel eluting with EtOAc to give the title compound. (8 mg, 10%). NMR: 0.7 (t, 3H), 1.52 (q, 2H), 2.80 (t, 2H), 2.85-2.89 (m, 2H), 3.19 (s, 3H), 3.18-3.22 (m, 2H), 3.30 (t, 2H), 4.52 (t, 2H), 4.98 (d, 1H), 5.10 (dd, 1H), 5.95-5.89 (m, 1H), 7.20 (d, 1H), 7.44 (t, 1H), 7.70 (s, 3H), 7.74 (d, 2H), 7.89 (d, 2H), 8.45 (d, 1H), 9.80 (s, 1H); m/z: 471.

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts were washed with water and brine
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was purified by chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-881f825a4f0d42bb963528782324699d
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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