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

HRID 1180889Notes

Reaction equation

HRID 1180889 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-9358a108a1fb42f3ace8d25a6270a994
Source dataset
uspto-grants-2007_10
Patent number
US07282588B2

Reaction notes

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