Dimethylformamide → HCID 69254702, compound

HRID 746798Notes

Reaction equation

HRID 746798 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]([S:10]([NH:13][C:14]1[CH:19]=[C:18]([C:20](O)=[O:21])[CH:17]=[CH:16][C:15]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][CH:31]=[CH:32][C:33]=2[NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])=[CH:25][CH:24]=1)(=[O:12])=[O:11])[CH3:9].[CH3:41][N:42](C=O)C.CN>ClCCl>[CH3:41][NH:42][C:20]([C:18]1[CH:17]=[CH:16][C:15]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[S:30][CH:31]=[CH:32][C:33]=3[NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:36])=[O:37])=[CH:25][CH:24]=2)=[C:14]([NH:13][S:10]([CH:8]([CH3:7])[CH3:9])(=[O:12])=[O:11])[CH:19]=1)=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 69253277HCID 69253277, compound

Product 1

HCID 69254702HCID 69254702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add oxalyl chloride (0.12 mmol) to a suspension of 2-(Propane-2-sulfonylamino)-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-carboxylic acid (0.1 mmol) and DMF (0.05 mmol) in dichloromethane at 0° C. Stir 1 h at RT. Concentrate to dryness under reduced pressure. Dissolve resultant residue in 3 ml CH2Cl2 and add (2.8 mmol) of MeNH2 (2M in THF). Concentrate the reaction to dryness and purify by flash chromatography (Silica gel- eluting with 5%MeOH/CH2Cl2). Concentrate the desired fractions to provide the title compound. MS (ES−): 534(M−1).

Workup

  1. concentrationConcentrate to dryness under reduced pressure
  2. dissolutionDissolve resultant residue in 3 ml CH2Cl2
  3. concentrationConcentrate
  4. customthe reaction to dryness
  5. custompurify by flash chromatography (Silica gel- eluting with 5%MeOH/CH2Cl2)
  6. concentrationConcentrate the desired fractions

Sources & evidence

ORD record
ord-58e6ad6dab384fdca2b7f232f15af9da
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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