p-Toluenesulfonic acid → HCID 54008973, compound

HRID 1383859Notes

Reaction equation

HRID 1383859 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][C:13]([C:14]([NH:16][NH2:17])=O)=[CH:12][CH:11]=1.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[C:54]([CH2:55][OH:56])=[N:53][CH:52]=[N:51]1.N1C=CC=CC=1CO>C(N(CC)CC)C>[CH3:49][N:50]1[C:54]([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:16]([C:14]([C:13]4[CH:18]=[CH:19][C:10]([F:9])=[CH:11][CH:12]=4)=[N:37][N:36]=3)[N:17]=2)=[N:53][CH:52]=[N:51]1

Participants

9

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 99724-FluorobenzohydrazideHCID 11130Triethylamine hydrochlorideHCID 11474PiconolHCID 11955BenzoylhydrazineHCID 581760Thiophene-3-boronic acidHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 54008973HCID 54008973, 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 4-fluorobenzhydrazide and triethylamine hydrochloride were used in Step b) instead of 1.1 equivalents of benzhydrazide, p-toluenesulphonic acid and triethylamine, and (2-methyl-2 H-1,2,4-triazol-3-yl)methanol (Example 66) was used in Step c) instead of 2-pyridylcarbinol. Data for the title compound: m.p. 268-269° C. (MeOH). 1H NMR (360 MHz, DMSO) δ3.92 (3 H, s), 5.79 (2 H, s), 7.46 (2 H, t, J=9 Hz), 7.70-7.74 (2 H, m), 8.01 (1 H, s), 8.19-8.21 (1 H, m), 8.45-8.49 (2 H, m), 8.68 (1 H, s). MS (ES+) 408 [MH]+. Anal. Found C, 55.90; H, 3.44; N, 24.02. C19H14N7FOS requires C, 56.01; H, 3.46; N, 24.07%.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-398afc2c1f324e7ebb3a04629f3d70b5
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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