Ethyl Acetate → HCID 59565321, compound

HRID 1962873Notes

Reaction equation

HRID 1962873 reaction equation
[CH3:1]C(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-].[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][CH:26]([S:36][CH3:37])[C:27]([NH:29][C:30]([CH2:34]O)([CH3:33])[C:31]#[CH:32])=[O:28])=[CH:20][CH:19]=2)#[CH:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.[Cl-].[Na+].O>[C:34]([C:30]([NH:29][C:27](=[O:28])[CH:26]([O:25][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:13]#[CH:14])=[CH:24]2)[S:36][CH3:37])([CH3:33])[C:31]#[CH:32])#[CH:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 595653502-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamideHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

Product 1

HCID 59565321HCID 59565321, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethyl-1-diazo-2-oxopropylphosphonate (0.109 g) in dry methanol (2 ml) was added at room temperature to a solution of crude 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-1-methyl-prop-2-ynyl)-2-methylsulfanyl-acetamide (0.125 g) from Stage 5 in methanol (5 ml). The reaction medium was cooled down to 0° C. and potassium carbonate (0.098 g) was added portion wise. The reaction mixture was allowed to warm up to room temperature and stirred for 5.5 hours and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure the resulting crude mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate) of N-(1-ethynyl-1-methyl-prop-2-ynyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a white solid (m.p.: 148-154° C.).

Workup

  1. temperatureto warm up to room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted thrice with ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration and concentration under reduced pressure the resulting crude mixture
  7. customwas purified by flash chromatography on silica gel (hexane/ethyl acetate) of N-(1-ethynyl-1-methyl-prop-2-ynyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a white solid (m.p.: 148-154° C.)

Sources & evidence

ORD record
ord-a4957ca2add54b339f06a57d8a30ec5e
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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