Dimethylformamide → HCID 57551206, compound

HRID 1644656Notes

Reaction equation

HRID 1644656 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:11]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([S:19](=[O:27])(=[O:26])[NH:20][C:21]4[S:22][CH:23]=[CH:24][N:25]=4)=[CH:15][CH:14]=3)[N:9]([CH2:28][C:29]([OH:31])=O)[N:8]=2)=[CH:4][CH:3]=1.C[N:35](C)C=O.C(Cl)Cl.C(Cl)(=O)C(Cl)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:11]=[C:10]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([S:19](=[O:27])(=[O:26])[NH:20][C:21]4[S:22][CH:23]=[CH:24][N:25]=4)=[CH:17][CH:18]=3)[N:9]([CH2:28][C:29]([NH2:35])=[O:31])[N:8]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 57551264HCID 57551264, compound

Product 1

HCID 57551206HCID 57551206, compound

Procedure

2-(3-(4-Chlorobenzyl)-5-(4-(N-thiazol-2-ylsulfamoyl)phenylamino)-1H-pyrazol-1-yl)acetic acid (30 mg, 0.00006 mol) was dissolved in N,N-Dimethylformamide (0.4 uL, 0.000005 mol) and methylene chloride (0.2 mL, 0.003 mol). Oxalyl chloride (7.6 uL, 0.000089 mol) was added and the reaction stirred 1 hour. The reaction was quenched by pouring it into 1.0 mL satd. ammonium hydroxide solution, neutralized with 1.0 N HCl, and extracted 2× with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate and evaporated to give the desired product, which was lyophilized from acetonitrile-water to provide a yellow powder.

Workup

  1. customThe reaction was quenched
  2. additionby pouring it into 1.0 mL
  3. extractionextracted 2× with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0a989cc5350a4865b0f792867a226d28
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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