HCID 57649659, compound → HCID 57649653, compound

HRID 39519Notes

Reaction equation

HRID 39519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:27]=[N:26][CH:25]=[CH:24][C:11]=1[C:12]([NH:14][O:15][CH2:16][C@H:17]1[CH2:21][O:20]C(C)(C)[O:18]1)=[O:13]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:27]=[N:26][CH:25]=[CH:24][C:11]=1[C:12]([NH:14][O:15][CH2:16][C@H:17]([OH:18])[CH2:21][OH:20])=[O:13]

Participants

3

Reactant 1

HCID 57649659HCID 57649659, compound

Product 1

HCID 57649653HCID 57649653, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

3-[(2-chloro-4-iodophenyl)amino]-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}isonicotinamide (100.00 mg, 0.198 mmol.) from the reaction described above was dissolved in acetic acid (1 ml) was heated at 90° C. for 2 h. The reaction was monitored by HPLC. After completion, acetic acid was removed and the crude was purified on Flashmaster II to obtain 40 mg (43%) of 3-[(2-chloro-4-iodophenyl)amino]-N-{[(2R)-2,3-dihydroxypropyl]oxy}isonicotinamide. LC/MS: [7.97 min; 464, 466 (M+1)]

Workup

  1. customAfter completion, acetic acid was removed
  2. customthe crude was purified on Flashmaster II

Sources & evidence

ORD record
ord-600433a7ef6249608a9b91534290cc69
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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