p-Toluenesulfonic acid → HCID 22457775, compound

HRID 1383861Notes

Reaction equation

HRID 1383861 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.[F:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=O.Cl.C(N(CC)CC)C.[C:28]([NH:36][NH2:37])(=O)[C:29]1[CH:34]=[CH:33]C=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:49][N:50]1[CH:54]=[N:53][C:52]([CH2:55][OH:56])=[N:51]1.N1C=CC=CC=1CO>C(N(CC)CC)C>[CH3:49][N:50]1[CH:54]=[N:53][C:52]([CH2:55][O:56][C:33]2[C:34]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[CH:29][C:28]3[N:14]([C:12]([C:11]4[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=4[F:9])=[N:37][N:36]=3)[N:15]=2)=[N:51]1

Participants

9

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 11130Triethylamine hydrochlorideHCID 11474PiconolHCID 11955BenzoylhydrazineHCID 1362882-FluorobenzhydrazideHCID 581760Thiophene-3-boronic acidHCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 22457775HCID 22457775, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This compound was prepared using the procedures described in Example 16, Steps a), b) and c) except that 3-thiophene boronic acid was used instead of 4-pyridyl boronic acid, di-lithium salt in Step a), 1.1 equivalents of 2-fluorobenzhydrazide and triethylamine hydrochloride were used in Step b) instead of 1.1 equivalents of benzhydrazide, p-toluenesulphonic acid and triethylamine, and (1-methyl-1 H-1,2,4-triazol-3-yl)methanol (Example 65) was used in Step c) instead of 2-pyridylcarbinol. Data for the title compound: m.p. 216-218° C. (MeOH). 1H NMR (360 MHz, DMSO) δ3.93 (3 H, s), 5.50 (2 H, s), 7.48-7.59 (2 H, m), 7.69-7.78 (2 H, m), 7.85 (1 H, dd, J=7, 2 Hz), 8.08-8.14 (1 H, m), 8.34 (1 H, dd, J=4, 2 Hz), 8.58 (1 H, s), 8.77 (1 H, s). MS (ES+) 408 [MH]+. Anal. Found C, 55.82; H, 3.57; N. 24.30. C19H14N7FOS requires C, 56.01; H, 3.46; N, 24.07%.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-5d1b0ab8eef94b6b8f0d451e21e17bee
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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