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1,4-Dioxane → HCID 131734353, compound

HRID 1505710
Notes
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Reaction equation

HRID 1505710 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][Si](C)(C)C)[CH:26]=4)=[N:23][CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:37]([CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])=[N+:38]=[N-:39].[CH2:45]1OCCOC1>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[N:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]5[N:39]=[N:38][N:37]([CH:40]([Si:41]([CH3:44])([CH3:43])[CH3:42])[CH3:45])[CH:32]=5)[CH:26]=4)=[N:21][CH:20]=3)[CH:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 150751Trimethylsilylmethyl AzideHCID 89924168HCID 89924168, compound2×

Product 1

HCID 131734353HCID 131734353, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalyst
HCID 962
Water
Solvent
2×

Procedure

A solution of copper sulfate pentahydrate (2.2 mg; 0.01 mmol; 0.04 eq.) in water (0.2 mL) was added to a mixture of 4-{4-[2-(3-Trimethylsilanylethynyl-phenyl)-pyrimidin-5-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (intermediate 19, 110 mg; 0.22 mmol; 1.0 eq.), azidomethyl-trimethyl-silane (36 μl; 0.24 mmol; 1.1 eq.) and D-(−)-isoascorbic acid sodium salt (9 mg; 0.04 mmol; 0.2 eq.) in Dioxane-1,4 (3 mL). The vial was sealed and stirred overnight at 8000. The reaction mixture was then diluted with water and extracted with EtOAc (three times). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica afforded the title compound as a beige solid (60 mg, 49%). 1H NMR (300 MHz, DMSO-d6) δ 9.18 (s, 2H), 8.88 (t, J=1.6 Hz, 1H), 8.57 (s, 1H), 8.54 (s, 1H), 8.34 (dt, J=8.0 Hz, 1.6 Hz, 1H), 8.16 (s, 1H), 7.96 (dt, J=8.0 Hz, 1.6 Hz, 1H), 7.60 (t, J=8.0 Hz, 1H), 4.48-4.38 (m, 1H), 4.11-4.03 (m, 4H), 2.94 (m, 2H), 2.09-2.05 (m, 2H), 1.88-1.74 (m, 2H), 1.43 (s, 9H), 0.13 (s, 9H). MS (ESI+): 559.5.

Workup

  1. customThe vial was sealed
  2. extractionextracted with EtOAc (three times)
  3. washCombined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-0d18d58fcf1341818182a633c6855354
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216991B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes