1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67155797, compound

HRID 2196727Notes

Reaction equation

HRID 2196727 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[NH:12][C:6]2=[N:7][CH:8]=[C:9]([NH2:11])[CH:10]=[C:5]2[CH:4]=1.[Cl:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:15][C:16]1[C:21]([C:22]([NH:11][C:9]2[CH:10]=[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:13])[F:14])[NH:12][C:6]3=[N:7][CH:8]=2)=[O:23])=[C:20]([F:25])[C:19]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidHCID 671560542-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Product 1

HCID 67155797HCID 67155797, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-amine (0.040 g, 0.199 mmol), 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.064 g, 0.219 mmol), EDCI (0.042 g, 0.219 mmol) and HOBt (0.027 g, 0.199 mmol) were dissolved in DMF (0.6 mL) and stirred at room temperature for 16 hours. The reaction mixture was directly purified by reverse phase HPLC to give 6-chloro-2-fluoro-3-(propylsulfonamido)-N-(2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.050 g, 52%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.91 (s, 1H), 10.99 (s, 1H), 9.96 (s, 1H), 8.60-8.56 (m, 1H), 8.56-8.52 (m, 1H), 7.54 (t, 1H), 7.44 (d, 1H), 7.10 (s, 1H), 3.21-3.12 (m, 2H), 1.76 (m, 2H), 0.99 (t, 3H); m/z (ES-MS) 479.1 (100.0%) [M+1].

Workup

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

Sources & evidence

ORD record
ord-88f3a369a78748618be69bfc894a48f0
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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