Triethylamine → HCID 59643088, compound

HRID 2251093Notes

Reaction equation

HRID 2251093 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:19](Cl)=[O:20])=[CH:4][CH:3]=1.Cl.[CH3:23][NH:24][O:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:26][O:25][N:24]([CH3:23])[C:19]([C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1)=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 59643072HCID 59643072, compound

Product 1

HCID 59643088HCID 59643088, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-fluoro-phenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl chloride, 25, (1.02 g, 3.15 mmol) in CH2Cl2 (20 mL) is added N,O-dimethylhydroxylamine hydrochloride salt (0.37 g, 3.80 mmol) and triethylamine (1.32 mL, 9.50 mmol). The mixture is allowed to stir at room temperature for 16 hours. The reaction is diluted with H2O and extracted three times with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (5% to 40% EtOAc/hexanes) to afford 660 mg of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.90 (s, 1H), 7.44 (dd, J=8.4, 5.9 Hz, 2H), 7.22 (dd, J=8.4, 5.9 Hz, 2H), 7.10 (s, 1H), 3.62 (s, 3H), 3.26 (s, 3H), 2.54 (s, 3H); ESI+ MS: m/z (rel intensity) 347.0 (100, M++H).

Workup

  1. extractionextracted three times with EtOAc
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is purified over silica (5% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ef09ef6f4ea14e5ea54168117f3c5538
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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