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Pyridine → HCID 69557498, compound

HRID 1934439
Notes
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Reaction equation

HRID 1934439 reaction equation
[CH3:1][O:2][C:3](=[O:32])[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]=[CH:22][C:21]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.[C:33](Cl)(=[O:37])[C:34](Cl)=[O:35].[N:39]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[C:7]2[C:16]([C:33](=[O:37])[C:34]([NH2:39])=[O:35])=[C:15]([CH2:17][CH3:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 69558384[[2-(methylthio)-6-ethyl-7-([1,1'-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester

Product 1

HCID 69557498HCID 69557498, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 187 mg (0.417 mmol) of [[2-(methylthio)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.11 mL of oxalyl chloride followed by 0.05 mL of pyridine. The mixture was stirred for 2 days then quenched into 4.0 mL of dilute ammonium hydroxide. The product was extracted into 5.0 mL of methylene chloride. The organic phase was dried with sodium sulfate and concentrated to 500 mg of yellow oil. The residue was purified by flash chromatography (5 g of silica, ethyl acetate) to provide 240 mg of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as an oil. nmr (300 MHz, CDCl3) δ0.82 (t, 3H), 2.52 (s, 3H), 2.59 (q, 2H), 3.77 (s, 3H), 5.00 (s, 2H), 5.40 (s, 2H), 5.68 (s, 1H), 6.54 (s, 1H), 6.85 (d, 1H), 7.1-7.6 (m, J=6.7, 8H)

Workup

  1. customthen quenched into 4.0 mL of dilute ammonium hydroxide
  2. extractionThe product was extracted into 5.0 mL of methylene chloride
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated to 500 mg of yellow oil
  5. customThe residue was purified by flash chromatography (5 g of silica, ethyl acetate)

Sources & evidence

ORD record
ord-60d718b6d2014fac8468554207b2c3a8
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06384041B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes