Triethylamine → HCID 67089053, compound

HRID 1943936Notes

Reaction equation

HRID 1943936 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([F:11])[C:5]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:40][C:41]1[CH:42]=[C:43]2[C:49]([O:50][CH2:51][CH3:52])=[N:48][N:47]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C:44]2=[N:45][CH:46]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]([C:8]([NH:40][C:41]2[CH:42]=[C:43]3[C:49]([O:50][CH2:51][CH3:52])=[N:48][N:47]([C:53]([O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[O:54])[C:44]3=[N:45][CH:46]=2)=[O:10])=[C:6]([F:11])[C:5]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidHCID 67088998HCID 67088998, compound

Product 1

HCID 67089053HCID 67089053, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.446 g, 1.51 mmol), EDCI (0.723 g, 3.77 mmol), and HOBt (0.578 g, 3.77 mmol) in DMF (6 mL) was stirred at room temperature for 25 minutes. tert-Butyl 5-amino-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.21 g, 0.755 mmol) was added to the reaction mixture, followed by the addition of Et3N (0.53 mL, 3.77 mmol). After stirring for 4 hours, the reaction mixture was diluted with EtOAc, washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give the crude material. The crude material was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2) to afford tert-butyl 5-(6-chloro-2-fluoro-3-(propylsulfonamido)benzamido)-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (90 mg, 22% yield).

Workup

  1. stirringAfter stirring for 4 hours
  2. washwashed with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude material
  6. customThe crude material was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-71e866e6fe384dc4bfb84dd59fc18135
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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