Ethyl Acetate → HCID 178509156, compound

HRID 255002Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[N:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:4]([CH2:7][NH:8][C:9](=[O:16])[C:10]2C=CC=NC=2)=[N:5][N:6]=1.NCC1C(=NNC2C=CC=C(F)C=2)C(N)=NN=1.Cl.C(Cl)(=O)C1C=CC=NC=1.[C:53]([O:56]CC)(=[O:55])[CH3:54]>>[NH2:1][C:2]1[C:3](=[N:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:4]([CH2:7][NH:8][C:9]([CH:10]=[CH:54][C:53]([OH:56])=[O:55])=[O:16])=[N:5][N:6]=1

Participants

Reactant 4

HCID 8857Ethyl Acetate

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

HCID 178509154HCID 178509154, compound

HCID 178510679HCID 178510679, compound

Product 1

HCID 178509156HCID 178509156, compoundYield 41%

Procedure

In a similar manner, N-{5-amino-4-[(3-fluorophenyl)hydrazono]4H-pyrazol-3-ylmethyl}nicotinamide was prepared by reacting 5-aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (60 mg, 0.25 mmole) with nicotinoyl chloride hydrochloride (46.3 mg, 0.26 mmole). The reaction was worked up by the addition of saline and ethyl acetate. The crude material was purified by preparative TLC (CH2Cl2:MeOH=9:1) to yield 36 mg (41%) of the title compound as a yellow powder. MS (m/z, ES+): 340 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 11.80 (br s, 1H), 9.01 (br s, 2H), 8.70 (d, 1H), 8.20 (d, 1H), 7.30-7.70 (m, 4H), 6.85-7.25 (m, 3H), 4.70 (br s, 2H).

Workup

customThe crude material was purified by preparative TLC (CH2Cl2:MeOH=9:1)

Sources & evidence

ORD record: ord-912d0977a85c41e5bc8e27a7395a7e54
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875728B2

Reaction notes

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