HCID 178433793, compound → HCID 178433795, compound

HRID 238713Notes

Reaction equation

HRID 238713 reaction equation
OC1C(N/N=[C:10]2/C(C)=N[N:13]([C:16]3C=C4C(=C[CH:24]=3)CCC4)[C:14]/2=O)=CC=CC=1C1OC(C(O)=O)=CC=1.[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35].C(NCC)C.[OH:44][C:45]1[C:50]([NH:51]/[N:52]=[C:53]2/[C:54]([CH3:69])=[N:55][N:56]([C:59]3[CH:68]=[CH:67][C:66]4[CH2:65]C[CH2:63][CH2:62][C:61]=4[CH:60]=3)[C:57]/2=[O:58])=[CH:49][CH:48]=[CH:47][C:46]=1[C:70]1[O:74][C:73]([C:75]([OH:77])=[O:76])=[CH:72][CH:71]=1>O1CCCC1>[CH2:14]([NH:13][CH2:16][CH3:24])[CH3:10].[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35].[OH:44][C:45]1[C:50]([NH:51]/[N:52]=[C:53]2/[C:54]([CH3:69])=[N:55][N:56]([C:59]3[CH:60]=[C:61]4[C:66](=[CH:67][CH:68]=3)[CH2:65][CH2:63][CH2:62]4)[C:57]/2=[O:58])=[CH:49][CH:48]=[CH:47][C:46]=1[C:70]1[O:74][C:73]([C:75]([OH:77])=[O:76])=[CH:72][CH:71]=1

Participants

4

Reactant 2

HCID 178433793HCID 178433793, compoundHCID 178433813HCID 178433813, compound

Product 1

HCID 178433795HCID 178433795, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-furan-2-carboxylic acid 16a (150 mg, 0.38 mmol) was suspended in 5 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added dropwise with diethylamine (49 mg, 0.67 mmol) to form a purple solution, and stirred for 2 hours at room temperature. The solid was precipitated from solution, filtered, then the filter cake was washed with tetrahydrofuran (1 mL×3) and dired in vacuo to obtain the title compound (Z)-5-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-furan-2-carboxylic acid bis-(diethylamine) 17 (163 mg, yield: 81.9%) as a dark red solid.

Workup

  1. customto form a dark red suspension
  2. customto form a purple solution
  3. customThe solid was precipitated from solution
  4. filtrationfiltered
  5. washthe filter cake was washed with tetrahydrofuran (1 mL×3) and dired in vacuo

Sources & evidence

ORD record
ord-2f915dab99fc44768b7e5ceaaa186f67
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

Loading…