Triethylamine → HCID 57649517, compound

HRID 2384901Notes

Reaction equation

HRID 2384901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH2:42])[CH:28]=[CH:29][C:30]=1[O:31][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:42][C:13]([C:11]2[S:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][C:10]=2[CH3:16])=[O:15])[CH:28]=[CH:29][C:30]=1[O:31][Si:32]([CH:36]([CH3:38])[CH3:37])([CH:39]([CH3:41])[CH3:40])[CH:33]([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10824737HCID 10824737, compoundHCID 57501693HCID 57501693, compound

Product 1

HCID 57649517HCID 57649517, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Suspend 5-(4-chloro-phenyl)-3-methyl-thiophene-2-carboxylic acid (2.13 g, 8.44 mmol) in CH2Cl2 (15 mL) and treat with oxalyl chloride (1.5 mL, 16.87 mmol), followed by the addition of DMF (2 drops). Stir the mixture at RT for 2 h and then evaporate down in vacuo. Dissolve the resulting solid material in CH2Cl2 (30 mL) and cool to 0° C. Add 3-methoxy-4-triisopropylsilanyloxy-phenylamine (2.62 g, 8.86 mmol) and Et3N (1.8 mL, 12.66 mol) in CH2Cl2 (10 mL) dropwise at 0° C. Stir the reaction at 0° C. for 10 min and at RT for 30 min. Dilute the reaction with CH2Cl2 (100 mL), wash with 0.1 M HCl (2×30 mL), 1.0 M NaOH (2×30 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 20% EtOAc/hexane to give 3.53 g (79%) of the title compound. LC-MS/ES m/z (37Cl) 531.2 [M+].

Workup

  1. customevaporate down in vacuo
  2. dissolutionDissolve the resulting solid material in CH2Cl2 (30 mL)
  3. temperaturecool to 0° C
  4. customdropwise at 0° C
  5. stirringStir
  6. customthe reaction at 0° C. for 10 min
  7. waitat RT for 30 min
  8. additionDilute
  9. washwash with 0.1 M HCl (2×30 mL), 1.0 M NaOH (2×30 mL)
  10. dry with materialdry over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate
  13. customPurify the crude material by chromatography
  14. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-baf281e03e2d4f3dad0483ce256ae994
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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