Ammonium Chloride → HCID 178509156, compound

HRID 2095169Notes

Reaction equation

HRID 2095169 reaction equation
[NH2:1][C:2]1[C:3](=[N:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:4]([CH2:7][NH:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[N:5][N:6]=1.NCC1C(=NNC2C=CC=C(F)C=2)C(N)=NN=1.[Cl-].[NH4+]>C(OCC)(=O)C>[NH2:1][C:2]1[C:3](=[N:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:4]([CH2:7][NH:8][C:9]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[O:15])=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 178509157HCID 178509157, compoundHCID 178510679HCID 178510679, compound

Product 1

HCID 178509156HCID 178509156, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner, N-{5-amino-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylmethyl}succinamic acid was prepared by reacting 5-aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (60 mg, 0.25 mmole) with succinic anhydide (40 mg, 0.4 mmole). The reaction was worked up by the addition of aqueous ammonium chloride solution and ethyl acetate. The crude material was purified by preparative TLC (CH2Cl2:CH3OH:H2O:HOAc=210:21:1.6:0.8) to yield 45 mg (51%) of the title compound as a yellow powder. MS (m/z, ES−): 333 (M−1, 42%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 8.23 (br s, 1H), 7.35-7.63 (m, 3H), 6.83-7.20 (m, 3H), 4.42 (s, 2H), 2.33 (m, 4H).

Workup

  1. customThe crude material was purified by preparative TLC (CH2Cl2:CH3OH:H2O:HOAc=210:21:1.6:0.8)

Sources & evidence

ORD record
ord-91be3a0e06fb45c6b295644ae15826ce
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

Loading…