1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide

HRID 2196721노트

반응식

HRID 2196721 반응식
[CH3:1][C:2]1[NH:11][C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[C:3]=1[CH3:12].[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>[CH3:1][C:2]1[NH:11][C:5]2=[N:6][CH:7]=[C:8]([NH:10][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:9]=[C:4]2[C:3]=1[CH3:12]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 671560582,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

생성물 1

HCID 67155730N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,3-Dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine (0.048 g, 0.298 mmol), 2,6-difluoro-3-(3-propylsulfonamido)benzoic acid (0.092 g, 0.328 mmol), EDCI (0.063 g, 0.328 mmol) and HOBt (0.040 g, 0.298 mmol) were dissolved in DMF (1.6 mL) and stirred at room temperature for 16 hours. The reaction mixture was directly purified by reverse phase HPLC to give N-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.059 g, 47%) as a solid. 1H NMR (400 MHz, d6-DMSO) 11.23 (s, 1H), 10.77 (s, 1H), 9.19 (br s, 1H), 8.27-8.09 (m, 2H), 7.59-7.39 (m, 1H), 7.28-7.10 (m, 1H), 3.17-2.95 (m, 2H), 2.32 (s, 3H), 2.15 (s, 3H), 1.84-1.65 (m, 2H), 0.98 (s, 3H); m/z (ES-MS) 423.2 (96.1%) [M+1].

후처리

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

출처 및 근거

ORD 기록
ord-4c6b9293e7504e0197043d56e2a0b796
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338452B2

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