Pyridine → HCID 69558654, compound

HRID 1934441Notes

Reaction equation

HRID 1934441 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]([F: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]([F: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 chlorideHCID 69558084HCID 69558084, compound

Product 1

HCID 69558654HCID 69558654, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 300 mg (0.770 mmol) of [[2-(methylthio)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.21 mL of oxalyl chloride followed by 0.09 mL of pyridine. The reaction was stirred for 2 days at ambient temperature then quenched into 4.0 mL of dilute ammonium hydroxide. The product was extracted into 4.0 mL of methylene chloride. The organic phase was washed with water, dried with sodium sulfate and concentrated to 430 mg of tan solid. The residue was purified by flash chromatography (45 g of silica, ethyl acetate) to provide 260 mg (73%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)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), 6.91 (d, 1H), 7.03 (d, 1H), 7.12 (dt, 1H), 7.47 (dt, 1H), 7.60 (s, 1H), 8.01 (s, 1H)

Workup

  1. customthen quenched into 4.0 mL of dilute ammonium hydroxide
  2. extractionThe product was extracted into 4.0 mL of methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to 430 mg of tan solid
  6. customThe residue was purified by flash chromatography (45 g of silica, ethyl acetate)

Sources & evidence

ORD record
ord-039f1ae3c7e54dcba2739b04d9013d6e
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

Loading…