Hydrochloric Acid → [3-(4-{[(phenylamino)carbonyl]amino}phenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid

HRID 28931Notes

Reaction equation

HRID 28931 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][CH:22]=[CH:23][C:16]=34)=[CH:13][N:12]([CH2:24][C:25]([OH:27])=[O:26])[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn].Cl.[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)C>[C:30]1([NH:36][C:37]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([C:10]3[C:14]([C:15]4[CH:20]=[CH:19][N:18]=[C:17]5[NH:21][CH:22]=[CH:23][C:16]=45)=[CH:13][N:12]([CH2:24][C:25]([OH:27])=[O:26])[N:11]=3)=[CH:6][CH:5]=2)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 5352426Tin atomHCID 68996956[3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid

Product 1

HCID 68996013[3-(4-{[(phenylamino)carbonyl]amino}phenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A heterogeneous mixture of [3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid (31.0 mmol), elemental tin dust (5.30 mmol), 6.0N aqueous hydrochloric acid (5.3 mL) and absolute ethanol (5.3 mL) was stirred at 70° C. for 1 h. The solution was filtered through Celite and concentrated in vacuo. The resulting aniline was dissolved in anhydrous pyridine (10 mL) and phenyl isocyanate (11.17 mmol) added dropwise. The reaction mixture was stirred at room temperature for 4 h. After concentration in vacuo, purification by Gilson reverse phase HPLC afforded the title compound as a white solid (93%). ESMS [M+H]+: 453.2

Workup

  1. filtrationThe solution was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting aniline was dissolved in anhydrous pyridine (10 mL)
  4. stirringThe reaction mixture was stirred at room temperature for 4 h
  5. concentrationAfter concentration
  6. customin vacuo, purification by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-ce085ef97fd64bb4883eed266e4f6520
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

Loading…