Pyridine → HCID 86567106, compound

HRID 1049872Notes

Reaction equation

HRID 1049872 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].N1C=CC=CC=1.[OH:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>CN(C1C=CN=CC=1)C.CC#N.C(Cl)Cl>[OH:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([NH:1][C:2]1[S:3][C:4]([S:10]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)(=[O:12])=[O:11])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8])=[O:29]

Participants

7

Reactant 3

HCID 1049PyridineHCID 74041Salicyloyl chlorideHCID 117703960HCID 117703960, compound

Product 1

HCID 86567106HCID 86567106, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-5-(morpholine-4-sulfonyl)-thiophene-3-carboxylic acid amide (150 mg, 0.51 mmol) is mixed with pyridine (63 μL, 0.77 mmol) and DMAP (15 mg, 0.12 mmol) in MeCN (1 mL). 2-Hydroxy-benzoyl chloride (103 mg, 0.65 mmol) is dissolved in 2 mL of MeCN and added to the reaction mixture. The resulting solution is stirred at 60° C. for 2 h, then diluted with DCM and finally washed with aqueous NaHCO3. The organic phase is evaporated to yield a residue which is purified by preparative chromatography to afford the desired product.

Workup

  1. additionadded to the reaction mixture
  2. washfinally washed with aqueous NaHCO3
  3. customThe organic phase is evaporated
  4. customto yield a residue which
  5. customis purified by preparative chromatography

Sources & evidence

ORD record
ord-d51e5bc51e9e4ca5a2bec4b7721de9d3
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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