6-Chloro-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxamide → 6-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (2,3-dihydroxy-propoxy)-amide

HRID 500518Notes

Reaction equation

HRID 500518 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:4]([C:17]([NH:19][O:20][CH2:21][C@H:22]2[CH2:26][O:25]C(C)(C)[O:23]2)=[O:18])[CH:3]=1>C(O)(=O)C.O>[OH:23][CH:22]([CH2:26][OH:25])[CH2:21][O:20][NH:19][C:17]([C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[F:16])=[O:18]

Participants

3

Reactant 1

HCID 594242046-Chloro-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxamide

Product 1

HCID 722805266-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (2,3-dihydroxy-propoxy)-amide

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

6-Chloro-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxamide (38 mg, 0.07 mmol) was heated at 90° C. in acetic acid/water (85%, 1.5 mL) for 2 hours. The mixture was concentrated and purified by flash chromatography to give the desired adduct. LC/MS [Method B: rt: 7.02 min; m/z: 483 (M+1)].

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8207f8c764c1484a9b9ace58f306b594
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

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