1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178434469, compound

HRID 1943916Notes

Reaction equation

HRID 1943916 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[F:12][C:13]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH2:28][F:29])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:30])[C:14]=1[C:15](O)=[O:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:12][C:13]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH2:28][F:29])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:30])[C:14]=1[C:15]([NH:11][C:8]1[CH:9]=[C:10]2[C:2]([CH3:1])=[N:3][NH:4][C:5]2=[N:6][CH:7]=1)=[O:16]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580953432,6-Difluoro-3-(3-fluoropropylsulfonamido)benzoic acidHCID 178434468HCID 178434468, compound

Product 1

HCID 178434469HCID 178434469, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine (0.100 g, 0.675 mmol, Example 4, Step B), 2,6-difluoro-3-(3-fluoropropylsulfonamido)benzoic acid (0.211 g, 0.709 mmol), EDCI (0.136 g, 0.709 mmol) and HOBt (0.091 g, 0.675 mmol) were dissolved in DMF (1.9 mL) and stirred at room temperature for 16 hours. The reaction mixture was purified by reverse phase HPLC to give 2,6-difluoro-3-(3-fluoropropylsulfonamido)-N-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (0.085 g, 29%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 13.22 (s, 1H), 11.05 (s, 1H), 9.93 (br s, 1H), 8.60-8.59 (m, 1H), 8.55-8.54 (m, 1H), 7.59-7.53 (m, 1H), 7.30-7.25 (m, 1H), 4.62 (t, 1H), 4.50 (t, 1H), 3.26-3.23 (m, 2H), 2.20-2.07 (m, 2H); m/z (ES-MS) 428.1 (100.0%) [M+1].

Workup

  1. customThe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8e90b7c98f97430ab6be0662da1b8114
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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