Dimethylformamide → HCID 67372485, compound

HRID 1676990Notes

Reaction equation

HRID 1676990 reaction equation
[NH2:1][C:2]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[S:13]([N:16]([CH3:21])CC(O)=O)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:22])=[CH:8][CH:7]=2)=[O:3].[C:23](Cl)(=[O:27])[C:24](Cl)=O.C[N:30](C=O)C.[NH4+].[OH-].CC(C)=O>ClCCl.CC(C)=O>[NH2:1][C:2]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[S:13]([N:16]([CH3:21])[C:23](=[O:27])[CH2:24][NH2:30])(=[O:14])=[O:15])=[CH:10][C:9]([Cl:22])=[CH:8][CH:7]=2)=[O:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10315576HCID 10315576, compoundHCID 86617444NH4OH acetone

Product 1

HCID 67372485HCID 67372485, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-{[2-(Aminocarbonyl)-5-chloro-1H-indol-3-yl]sulfonyl}-N-methylglycine from Example 56 (10 mg, 0.029 mmol) in 1 mL of dichloromethane at room temperature was added oxalyl chloride (0.3 mL), followed by DMF (ca. 0.020 mL). After 20 minutes, the homogeneous mixture was concentrated in vacuo to give a yellow solid. This was taken up in 1 mL of acetone, and a solution of 10% NH4OH/acetone (2 mL) was added, whereupon a white precipitate formed. After two minutes, the solvent was decanted off, and the resulting solid was maintained in vac o until dry. Purification by preparative reversed phase HPLC provided the titled compound as a white solid. ESI+ MS: 345.2 [M+H]+.

Workup

  1. concentrationthe homogeneous mixture was concentrated in vacuo
  2. customto give a yellow solid
  3. customformed
  4. waitAfter two minutes
  5. customthe solvent was decanted off
  6. temperaturethe resulting solid was maintained in vac o
  7. customuntil dry
  8. customPurification by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-56a0e9f811604f9d9a8470055a0a69a0
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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