O-(Trimethylsilyl)hydroxylamine → HCID 136054509, compound

HRID 606515Notes

Reaction equation

HRID 606515 reaction equation
[CH3:1][CH:2]([CH3:35])/[CH:3]=[CH:4]/[S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[O:23])[CH:15]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].C[Si](C)(C)[O:38][NH2:39]>C1COCC1>[OH:38][NH:39][CH:3]([CH:2]([CH3:35])[CH3:1])[CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[O:23])[CH:15]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 136054480HCID 136054480, compound

Product 1

HCID 136054509HCID 136054509, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(4′-{[(1E)-3-methylbut-1-en-1-yl]sulfonyl}biphenyl-3-yl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 106 (0.180 g, 0.369 mmol) in THF (4 mL) was added O-(trimethylsilyl)hydroxylamine (0.271 mL, 2.22 mmol) at room temperature, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate-diethyl ether to give the title compound as a white powder (0.125 g, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-720fb143930a403a930ad27d297e8a49
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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