1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178522374, compound

HRID 1943915Notes

Reaction equation

HRID 1943915 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.[F:14][C:15]1[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH2:30][F:31])(=[O:27])=[O:26])=[CH:22][CH:21]=[C:20]([F:32])[C:16]=1[C:17](O)=[O:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH:1]1([C:4]2[C:12]3[C:7](=[N:8][CH:9]=[C:10]([NH:13][C:17](=[O:18])[C:16]4[C:20]([F:32])=[CH:21][CH:22]=[C:23]([NH:24][S:25]([CH2:28][CH2:29][CH2:30][F:31])(=[O:26])=[O:27])[C:15]=4[F:14])[CH:11]=3)[NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580953432,6-Difluoro-3-(3-fluoropropylsulfonamido)benzoic acidHCID 178508013HCID 178508013, compound

Product 1

HCID 178522374HCID 178522374, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyclopropyl-1H-pyrazolo[3,4-b]pyridin-5-amine (0.024 g, 0.138 mmol), 2,6-difluoro-3-(3-fluoropropylsulfonamido)benzoic acid (0.045 g, 0.151 mmol), EDCI (0.029 g, 0.151 mmol) and HOBt (0.019 g, 0.138 mmol) were dissolved in DMF (0.52 mL) and stirred at room temperature for 16 hours. The reaction mixture was purified by reverse phase HPLC to give N-(3-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(3-fluoropropylsulfonamido)benzamide (0.031 g, 50%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 13.17 (s, 1H), 11.06 (s, 1H), 9.92 (br s, 1H), 8.63 (s, 1H), 8.56 (s, 1H), 7.60-7.54 (m, 1H), 7.28 (t, 1H), 4.62 (t, 1H), 4.51 (t, 1H), 3.29-3.23 (m, 3H), 2.33-2.26 (m, 1H), 2.19-2.09 (m, 2H), 1.01-0.93 (m, 3H); m/z (ES-MS) 454.2 (100.0%) [M+1].

Workup

  1. customThe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d23ca90875bb47b491b887bed265092f
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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