Water → HCID 56645465, compound

HRID 2040841Notes

Reaction equation

HRID 2040841 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH2:13][C:12]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22]([CH3:29])[N:21]=1.C(N(CC)CC)C.O>CN(C)C(=O)C>[CH3:29][C:22]1[N:21]=[C:20]([N:16]2[CH2:17][CH2:18][C:12]3([O:11][N:10]=[C:9]([C:8]#[C:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:13]3)[CH2:14][CH2:15]2)[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 574938083-(Phenylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene

Product 1

HCID 56645465HCID 56645465, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of Compound 1c (50 mg, 0.21 mmol), 2-chloro-6-methyl-3-nitropyridine (39.5 mg, 0.23 mmol) and triethylamine (31.9 μL, 0.23 mmol) in N,N-dimethylacetamide (1.14 mL) was stirred at r.t. for 24 h and poured into water. The aqueous layer was extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by automated flash chromatography (SP1®TM-Biotage) eluting with a Petroleum Ether-Me2CO 95:5 mixture. A further purification with CH2Cl2 as eluent afforded 47.7 mg of the title compound (67.7%) as yellow solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness in vacuo
  5. customThe crude product was purified by automated flash chromatography (SP1®TM-Biotage)
  6. washeluting with a Petroleum Ether-Me2CO 95:5 mixture
  7. customA further purification with CH2Cl2 as eluent

Sources & evidence

ORD record
ord-28667eb264e942f19f69b2d613363774
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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