1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67155940, compound

HRID 2196711Notes

Reaction equation

HRID 2196711 reaction equation
[CH2:1]([C:3]1[NH:12][C:6]2=[N:7][CH:8]=[C:9]([NH2:11])[CH:10]=[C:5]2[CH:4]=1)[CH3:2].[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>[CH2:1]([C:3]1[NH:12][C:6]2=[N:7][CH:8]=[C:9]([NH:11][C:16](=[O:17])[C:15]3[C:19]([F:30])=[CH:20][CH:21]=[C:22]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[C:14]=3[F:13])[CH:10]=[C:5]2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 67155914HCID 67155914, compound

Product 1

HCID 67155940HCID 67155940, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-1H-pyrrolo[2,3-b]pyridin-5-amine (0.100 g, 0.62 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.182 g, 0.65 mmol), EDCI (0.125 g, 0.65 mmol) and HOBt (0.084 g, 0.65 mmol) were dissolved in DMF (1.5 mL) and stirred at room temperature overnight. The solution was then directly purified by reverse phase HPLC to afford N-(2-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.061 g, 23% yield). 1H NMR (400 MHz, d6-DMSO) δ 11.46 (s, 1H), 10.75 (s, 1H), 9.79 (br s, 1H), 8.26-8.25 (m, 1H), 8.19-8.18 (m, 1H), 7.56-7.50 (m, 1H), 7.24 (t, 1H), 6.18-6.17 (m, 1H), 3.13-3.09 (m, 2H), 2.74 (q, 2H), 1.77 (sx, 2H), 1.28 (t, 3H), 0.99 (t, 3H); m/z (ES-MS) 423.2 (100.0%) [M+1].

Workup

  1. customThe solution was then directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-34af4143eb9344e68ebb91da0b9af99d
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…