Diisopropylethylamine → HCID 56675558, compound

HRID 2196690Notes

Reaction equation

HRID 2196690 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](C2C=C3N=CNC3=NC=2)[C:5]([F:12])=[C:6]([C:10]=1[F:11])[C:7]([NH2:9])=[O:8].[CH:22]1([S:25](Cl)(=[O:27])=[O:26])[CH2:24][CH2:23]1.C([N:32]([CH:35]([CH3:37])C)[CH2:33][CH3:34])(C)C>C(Cl)Cl.[Cl-].[Na+].O>[CH:22]1([S:25]([NH:1][C:2]2[C:10]([F:11])=[C:6]([C:5]([F:12])=[CH:4][CH:3]=2)[C:7]([NH:9][C:10]2[CH:6]=[C:37]3[CH:34]=[CH:33][NH:32][C:35]3=[N:1][CH:2]=2)=[O:8])(=[O:27])=[O:26])[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 178513704HCID 178513704, compound

Product 1

HCID 56675558HCID 56675558, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 5 mL flask was charged with 5-amino-2,6-difluoro-(3H-imidazo[4,5-b]pyridin-6-yl)benzamide (30 mg, 0.1 mmol), cyclopropyl sulfonyl chloride (10 mg, 0.1 mmol) and diisopropylethylamine (40 μL) in CH2Cl2 (1 mL). This mixture was stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine, extracted with EtOAc (2×), extracts washed with water (1×), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified via silica gel chromatography using an ISCO system (10% MeOH/DCM) to give the title compound (14 mg, 30%). m/z (LC-MS) M+1=393.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washextracts washed with water (1×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-28dbef0c12264ab7bfcf282d2cac5a00
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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