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Hydrochloric Acid → 4-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid

HRID 640699
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HRID 640699 반응식
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12](OC)=[O:13])=[N:10][CH:9]=[C:8]2[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:18][C:7]=12)[CH3:2].[NH2:27][OH:28].[OH-].[Na+].Cl>CO>[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]([NH:27][OH:28])=[O:13])=[N:10][CH:9]=[C:8]2[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:18][C:7]=12)[CH3:2]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 686652681h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-[(1e)-2-ethoxyethenyl]-1-[(4-fluorophenyl)methyl]-,methyl ester

생성물 1

HCID 159570544-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid수율 100.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To methyl 4-[(E)-2-ethoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.1 g, 0.28 mmol) in methanol (10 mL) were added hydroxylamine (1 mL, 50% in water, 15.2 mmol) and sodium hydroxide (63.8 mg, 1.59 mmol). The mixture was stirred at room temperature for 2 h, and 4N hydrochloric acid (0.5 mL, 1.9 mmol) was added. The mixture was concentrated to provide 100 mg of the title compound that was used without further purification in the next step. 1H NMR (DMSO-d6) δ ppm 11.76 (d, 1H, J=1.9 Hz), 8.88 (d, 1H, J=1.9 Hz), 8.60 (s, 1H), 7.83 (d, 1H, J=3.0 Hz), 7.31 (t, 2H, J=8.9 Hz), 7.22 (d, 1H, J=13.2 Hz), 7.05 (t, 2H, J=8.9 Hz), 6.82 (d, 1 H, J=3.0 Hz), 6.66 (d, 1 H, J=13.2 Hz), 5.54 (s, 2H), 3.96 (q, 2H, J=7.0 Hz), 1.28 (t, 3H, J=7.0 Hz). LCMS (APCl, M+H+): 356.

후처리

  1. concentrationThe mixture was concentrated

출처 및 근거

ORD 기록
ord-a1cd88a7ca054135bb84867581177f98
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07692014B2

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