1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178461065, compound

HRID 1943920Notes

Reaction equation

HRID 1943920 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][OH:12])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:13][C:14]1[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])=[CH:21][CH:20]=[C:19]([F:30])[C:15]=1[C:16](O)=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:13][C:14]1[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:25])=[O:26])=[CH:21][CH:20]=[C:19]([F:30])[C:15]=1[C:16]([NH:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][OH:12])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1)=[O:17]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 178508016HCID 178508016, compound

Product 1

HCID 178461065HCID 178461065, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5-Amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (0.040 g, 0.675 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.071 g, 0.256 mmol), EDCI (0.049 g, 0.256 mmol) and HOBt (0.033 g, 0.244 mmol) were dissolved in DMF (0.53 mL) and stirred at room temperature for 16 hours. The reaction mixture was directly purified by reverse phase HPLC to give 2,6-difluoro-N-(3-(hydroxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.051 g, 49%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 13.37 (s, 1H), 11.05 (s, 1H), 9.93 (br s, 1H), 8.74 (d, 1H), 8.58 (d, 1H), 7.58-7.52 (m, 1H), 7.26 (t, 1H), 5.36 (t, 1H), 4.78 (d, 2H), 3.12 (m, 2H), 1.77 (m, 2H), 1.00 (t, 3H); m/z (ES-MS) 426.1 (98.0%) [M+1].

Workup

  1. customThe reaction mixture was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9d999af1ea6148cfb5dcc912dd6d6f23
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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