Triethylamine → HCID 178504186, compound

HRID 1525338Notes

Reaction equation

HRID 1525338 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:10])=[NH:9].C[O:12][CH:13]=[C:14]([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15](OC)=O.C(N(CC)CC)C>CO>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:10]=[C:13]([OH:12])[C:14]([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12403615Pyridine-2-carboximidamide hydrochlorideHCID 53914070Methyl 2-(methoxymethylene)-4-(trimethylsilyl)but-3-ynoate

Product 1

HCID 178504186HCID 178504186, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound 37-b (15 g, 71 mmol), compound 37-h (12.2 g, 77.8 mmol), triethylamine (21.4 g, 212 mmol) in methanol (200 mL) was stirred overnight at room temperature. The residue obtained from removal of the solvent was purified by flash chromatography (DCM) to afford compound 37-i (7.5 g, 39%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.668-8.649 (m, 1H), 8.428-8.395 (m, 1H), 8.257 (s, 1H), 7.937-7.880 (m, 1H), 7.517-7.471 (m, 1H), 0.285 (s, 9H). LC-MS (ESI): 270 [M+H]+

Workup

  1. customThe residue obtained from removal of the solvent
  2. customwas purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-1a3cd87c7c62411ba8a7f50510f5fcae
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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