p-Toluenesulfonic acid → HCID 57438968, compound

HRID 1383860Notes

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[CH:54]=[N:53][C:52]([CH2:55][OH:56])=[N:51]1.N1C=CC=CC=1CO>>[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: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:51]1

Participants

Reactant 7

HCID 6101p-Toluenesulfonic acid

HCID 99724-Fluorobenzohydrazide

HCID 11130Triethylamine hydrochloride

HCID 11474Piconol

HCID 11955Benzoylhydrazine

HCID 581760Thiophene-3-boronic acid

HCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 57438968HCID 57438968, compound

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 triethylmine, 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. 254-255° C. (MeOH). 1H NMR (360 MHz, DMSO) δ3.89 (3 H, s), 5.61 (2 H, s), 7.46 (2 H, t, J=9 Hz), 7.71 (1 H, dd, J=5, 3 Hz), 7.80 (1 H, dd, J=5, 1 Hz), 8.28-8.29 (1 H, m), 8.51-8.56 (3 H, m), 8.67 (1 H, s). MS (ES+) 408 [MH]+. Anal. Found C, 55.88; H, 3.40; N, 23.98. C19H14N7FOS requires C, 56.01; H, 3.46; N, 24.07%.

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-d686de26a3e141dc9f25b37c44024b6c
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255305B1

Reaction notes

Loading…