Sodium bis(trimethylsilyl)amide → HCID 10257407, compound

HRID 1785106Notes

Reaction equation

HRID 1785106 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][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:24][C:25]1[CH:33]=[C:32]([C:34]#[C:35][CH2:36][O:37][CH:38]([CH3:40])[CH3:39])[C:28]2[O:29][CH2:30][O:31][C:27]=2[C:26]=1[NH2:41].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C>[Cl:24][C:25]1[CH:33]=[C:32]([C:34]#[C:35][CH2:36][O:37][CH:38]([CH3:39])[CH3:40])[C:28]2[O:29][CH2:30][O:31][C:27]=2[C:26]=1[NH:41][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][O:21][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 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 68882953HCID 68882953, compound

Product 1

HCID 10257407HCID 10257407, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-(3-isopropoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (174 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 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 (222 mg, 66%) as a pale yellow solid; NMR Spectrum:(DMSOd6) 1.15 (d, 6H), 1.97 (quintet, 2H), 2.39 (m, 4H), 2.47 (t, 2H), 3.59 (m, 4H), 3.80 (m, 1H), 3.93 (s, 3H), 4.20 (t, 2H), 4.40 (s, 2H), 6.16 (s, 2H), 7.14 (s, 1H), 7.19 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.50 (s, 1H); Mass Spectrum: M+H+ 569/571

Workup

  1. customThis was prepared
  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-7964d59c0c7649a787bd8ee1409aa931
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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