Hydrochloric Acid → HCID 69016663, compound

HRID 1455070Notes

Reaction equation

HRID 1455070 reaction equation
[F-].[K+].[OH:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][C:21]4[N:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=4)[CH:16]=3)[O:11]2)[CH:7]=[CH:8][CH:9]=1.Cl[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][N:34]=1.Cl>CN(C=O)C>[N+:39]([C:36]1[CH:37]=[CH:38][C:33]([O:3][C:4]2[CH:5]=[C:6]([CH:10]3[CH2:19][CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20][C:21]5[N:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=5)[CH:16]=4)[O:11]3)[CH:7]=[CH:8][CH:9]=2)=[N:34][CH:35]=1)([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 783082-Chloro-5-nitropyridineHCID 522689Potassium FluorideHCID 69018043HCID 69018043, compound

Product 1

HCID 69016663HCID 69016663, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium fluoride (42 mg) was added into a solution of N-{6-[2-(3-hydroxy-phenyl)chroman-6-yloxy]pyridin-3-yl}methanesulfonamide (100 mg) in dry DMF (1 ml). After stirring the resulting mixture at 120° C. for 30 minutes 2-chloro-5-nitropyridine (40 mg) was added. The reaction mixture was stirred for a further 30 minutes at 120° C. After cooling into room temperature 1 M HCl-solution was added and formed precipitate was filtered. N-(6-{2-[3-(5-Nitropyridin-2-yloxy)phenyl]-chroman-6-yloxy}pyridin-3-yl) methanesulfonamide was purified by column chromatography using 1:1 mixture of ethyl acetate and heptane as eluant. 1H NMR (300 MHz, d6-DMSO) δ: 9.64 (s, 1H), 9.04 (d, 1H, J 2.9 Hz), 8.63 (dd, 1H, J 2.9, 9.1 Hz), 7.98 (d, 1H, J 2.7 Hz), 7.66 (dd, 1H, J 2.7, 8.8 Hz), 7.52 (t, 1H, J 7.7 Hz), 7.39 (d, 1H, J 7.7 Hz), 7.31 (s, 1H), 7.27 (d, 1H, J 9.1 Hz), 7.22-7.19 (m, 1H), 6.96 (d, 1H, J 8.8 Hz), 6.89-6.85 (m, 3H), 5.17 (d, 1H, J 7.8 Hz), 2.97 (s, 3H), 2.98-2.92 (m, 1H), 2.76-2.69 (m, 1H) 2.28-2.19 (m, 1H), 2.02-1.97 (m, 1H).

Workup

  1. additionwas added
  2. additionwas added
  3. customformed precipitate
  4. filtrationwas filtered
  5. customN-(6-{2-[3-(5-Nitropyridin-2-yloxy)phenyl]-chroman-6-yloxy}pyridin-3-yl) methanesulfonamide was purified by column chromatography
  6. addition1:1 mixture of ethyl acetate and heptane as eluant

Sources & evidence

ORD record
ord-31e02b60a6564bfc825a419789d58ceb
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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