Sodium bis(trimethylsilyl)amide → HCID 10077301, compound

HRID 1785123Notes

Reaction equation

HRID 1785123 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][F:26])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:27][C:28]1[CH:36]=[C:35]([C:37]#[C:38][CH2:39][CH2:40][O:41][CH3:42])[C:31]2[O:32][CH2:33][O:34][C:30]=2[C:29]=1[NH2:43].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C>[Cl:27][C:28]1[CH:36]=[C:35]([C:37]#[C:38][CH2:39][CH2:40][O:41][CH3:42])[C:31]2[O:32][CH2:33][O:34][C:30]=2[C:29]=1[NH:43][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][F:26])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 68881321HCID 68881321, compoundHCID 86597574HCID 86597574, compound

Product 1

HCID 10077301HCID 10077301, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared by the method described in example 4 using 4-chloro-7-{3-[4-(2-fluoroethyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline (200 mg, 0.52 mmol), 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (146 mg, 0.57 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.10 ml) in DMF (3 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (187 mg, 60%) as colourless solid, NMR Spectrum:(CDCl3) 2.10 (quintet, 2H), 2.57 (m, 8H), 2.67 & 2.72 (dt, 2H), 2.74 (t, 2H), 3.41 (s, 3H), 3.60 (t, 2H), 3.98 (s, 3H), 4.23 (t, 2H), 4.51 & 4.63 (dt, 2H), 6.06 (s, 2H), 6.85 (s, 1H), 7.04 (s, 1H), 7.08 (s, 1H), 7.28 (s, 1H), 8.61 (s, 1H); Mass Spectrum: M+H+ 600/602

Workup

  1. customThis was prepared by the method
  2. customThe crude product was purified by column chromatography on silica using
  3. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-6b83045e29e547b7bec799a4143f6340
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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