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Sodium bis(trimethylsilyl)amide → HCID 68881132, compound

HRID 1785145
Notes
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Reaction equation

HRID 1785145 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]([CH3:24])[CH2:20][C:19]3=[O:25])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:26][C:27]1[C:32]2[O:33][CH2:34][O:35][C:31]=2[C:30]([C:36]#[C:37][CH2:38][NH:39][C:40](=[O:44])[N:41]([CH3:43])[CH3:42])=[CH:29][C:28]=1[Cl:45].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C>[Cl:45][C:28]1[CH:29]=[C:30]([C:36]#[C:37][CH2:38][NH:39][C:40](=[O:44])[N:41]([CH3:42])[CH3:43])[C:31]2[O:35][CH2:34][O:33][C:32]=2[C:27]=1[NH:26][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]([CH3:24])[CH2:20][C:19]3=[O:25])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 68881428HCID 68881428, compoundHCID 866015631-{3-[(4-Chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one

Product 1

HCID 68881132HCID 68881132, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

This was prepared by the method described in example 4 but using 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (140 mg, 0.38 mmol), N′-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N,N-dimethylurea (125 mg, 0.42 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 0.81 ml) in DMF (2 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent. There was thus obtained the title compound (193 mg, 81%) as a pale yellow solid; NMR Spectrum:(DMSOd6) 2.03 (quintet, 2H), 2.20 (s, 3H), 2.59 (t, 2H), 2.81 (s, 6H), 2.91 (s, 2H), 3.33 (t, 2H), 3.48 (t, 2H), 3.94 (s, 3H), 4.10 (d, 2H), 4.14 (t, 2H), 6.14 (s, 2H), 6.82 (t, 1H), 7.07 (s, 1H), 7.16 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.49 (s, 1H); Mass Spectrum: M+H+ 624/626.

Workup

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

Sources & evidence

ORD record
ord-cbc5759bd06e4d7e9967c05197de00e0
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07504408B2

Reaction notes

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