Methylamine → HCID 69253638, compound

HRID 746799Notes

Reaction equation

HRID 746799 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:23][CH:24]=[CH:25][C:26]=2[NH:27][S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[CH:18][CH:17]=1)#[N:6].[CH3:34][NH2:35]>ClCCl>[CH3:34][NH:35][C:13]([C:11]1[CH:10]=[CH:9][C:8]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[S:23][CH:24]=[CH:25][C:26]=3[NH:27][S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[CH:20][CH:21]=2)=[C:7]([C:5]#[N:6])[CH:12]=1)=[O:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 24769562HCID 24769562, compound

Product 1

HCID 69253638HCID 69253638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Add thionyl chloride (0.2 mmol) to a suspension of 2-Cyano-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-carboxylic acid (0.1 mmol) in dichloromethane at RT. Stir mixture for 1 h at 50° C. and concentrate to dryness under reduced pressure. Add to the resultant residue 0.5 mmol MeNH2 (2M in THF). Concentrate the reaction to dryness and purify with flash chromatography (Silica gel-5%MeOH/CH2Cl2). Concentrate the desired fractions to provide the title compound. MS (ES−):438 (M−1).

Workup

  1. concentrationconcentrate to dryness under reduced pressure
  2. concentrationConcentrate
  3. customthe reaction to dryness
  4. custompurify with flash chromatography (Silica gel-5%MeOH/CH2Cl2)
  5. concentrationConcentrate the desired fractions

Sources & evidence

ORD record
ord-cfbbf61981bf4858939ede6e323379fd
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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