Diisopropylethylamine → HCID 66749237, compound

HRID 537074Notes

Reaction equation

HRID 537074 reaction equation
[I:1][C:2]1[N:3]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][NH:9][N:8]=1.CCN(C(C)C)C(C)C.[CH3:32][Si:33]([CH2:36][CH2:37][O:38][CH2:39]Cl)([CH3:35])[CH3:34]>CN(C=O)C>[I:1][C:2]1[N:3]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:39][O:38][CH2:37][CH2:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178474061HCID 178474061, compound

Product 1

HCID 66749237HCID 66749237, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{4-[4-iodo-5-(1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (6.2 g, 15 mmol) in DMF (60 mL) was added DIEA (4.0 mL, 23.0 mmol). The reaction mixture was allowed to stir at rt for 2 h and then SEM-Cl (4.1 mL, 23.0 mmol) was added. The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give N-{4-[4-iodo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (2.7 g) plus another SEM regioisomer (1.2 g).

Workup

  1. stirringto stir at rt overnight
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b3a6fd505a35402788170d231b7164fb
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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