1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178461051, compound

HRID 1943966Notes

Reaction equation

HRID 1943966 reaction equation
[CH:1]1([C:4]2[C:12]3[C:7](=[N:8][CH:9]=[C:10]([NH2:13])[CH:11]=3)[NH:6][N:5]=2)[CH2:3][CH2:2]1.[Cl:14][C:15]1[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])=[CH:22][CH:21]=[C:20]([F:31])[C:16]=1[C:17](O)=[O:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[Cl:14][C:15]1[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH3:30])(=[O:26])=[O:27])=[CH:22][CH:21]=[C:20]([F:31])[C:16]=1[C:17]([NH:13][C:10]1[CH:11]=[C:12]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:5][NH:6][C:7]2=[N:8][CH:9]=1)=[O:18]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580953612-Chloro-6-fluoro-3-(propylsulfonamido)benzoic acidHCID 178508013HCID 178508013, compound

Product 1

HCID 178461051HCID 178461051, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Cyclopropyl-1H-pyrazolo[3,4-b]pyridin-5-amine (0.0744 g, 0.427 mmol), 2-chloro-6-fluoro-3-(propylsulfonamido)benzoic acid (0.139 g, 0.470 mmol), EDCI (0.0901 g, 0.470 mmol), and HOBt (0.0635 g, 0.470 mmol) were dissolved in DMF (2 mL) and stirred for 24 hours. The reaction mixture was diluted with ethyl acetate and washed with water (4 X), saturated aqueous sodium bicarbonate solution (2×), and brine, dried over sodium sulfate and concentrated. The crude product was triturated with 1:1 DCM/Et2O to afford 2-chloro-N-(3-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-6-fluoro-3-(propylsulfonamido)benzamide (128 mg, 66% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) 813.21 (s, 1H), 11.08 (s, 1H), 9.74 (s, 1H), 8.66 (s, 1H), 8.55 (s, 1H), 7.59-7.63 (m, 1H), 7.40-7.46 (m, 1H), 3.11-3.15 (m, 2H), 2.29-2.31 (m, 1H), 1.79-1.80 (m, 2H), 0.95-1.00 (m, 7H); MS (APCI-neg) m/z=452.2, 454.1 (M+H).

Workup

  1. washwashed with water (4 X), saturated aqueous sodium bicarbonate solution (2×), and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was triturated with 1:1 DCM/Et2O

Sources & evidence

ORD record
ord-c508cd71b1f54b8a831a176cf2ec4621
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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