Pyridine → HCID 69558667, compound

HRID 1934445Notes

Reaction equation

HRID 1934445 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[C:7]2[CH:16]=[C:15]([CH2:17][CH3:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.[C:28](Cl)(=[O:32])[C:29](Cl)=[O:30].[N:34]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[C:7]2[C:16]([C:28](=[O:32])[C:29]([NH2:34])=[O:30])=[C:15]([CH2:17][CH3:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chloride2×HCID 69558414HCID 69558414, compound

Product 1

HCID 69558667HCID 69558667, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 150 mg (0.371 mmol) of [[2-(methylthio)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.10 mL of oxalyl chloride followed by 0.04 mL of pyridine. The reaction stirred at ambient temperature and was monitored by nmr for conversion to product. Additional oxalyl chloride (0.030 mL) was added after 24 hours. After 48 hours, the reaction was quenched into 4.0 mL of dilute ammonium hydroxide and the product was extracted into 5.0 mL of methylene chloride. The organic phase was washed with water, dried with sodium sulfate and concentrated to 400 mg of yellow solid. The residue was purified by flash chromatography (38 g of silica, ethyl acetate) to provide 109 mg (62%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a solid. nmr (300 MHz, dmso-d6) δ1.00 (t, 3H), 2.45 (s, 3H), 2.90 (q, 2H), 3.65 (s, 3H), 4.97 (s, 2H), 5.52 (s, 2H), 7.01 (m, 1H), 7.31 .(m, 3H), 7.60 (s, 1H), 8.02 (s, 1H)

Workup

  1. customthe reaction was quenched into 4.0 mL of dilute ammonium hydroxide
  2. extractionthe product was extracted into 5.0 mL of methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to 400 mg of yellow solid
  6. customThe residue was purified by flash chromatography (38 g of silica, ethyl acetate)

Sources & evidence

ORD record
ord-98650cac56e24598ad1f0ebd7621b5ec
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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