Morpholine → 3-(2-Fluoro-4-iodo-phenylamino)-6-morpholin-4-yl-pyridazine-4-carboxylic acid

HRID 2404221Notes

Reaction equation

Cl[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]([OH:19])=[O:18])[CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CN(C=O)C.CCOCC>[F:16][C:10]1[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=1[NH:8][C:5]1[N:6]=[N:7][C:2]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:3][C:4]=1[C:17]([OH:19])=[O:18]

Participants

Conditions

Temperature: 135 °C

Procedure

To mixture of 6-chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (34 mg, 0.09 mmol) in DMF was added morpholine (37.7 mg, 0.43 mmol). The mixture was heated at 135° C. for 3.5 h. The mixture was diluted with ether and extracted with NaOH (1N). The aqueous layer was acidified by concentrated HCl. The desired product was precipitated and was collected by vacuum filtration. LC/MS [5.51 min; 445 (M+1)].

Workup

extractionextracted with NaOH (1N)
customThe desired product was precipitated
filtrationwas collected by vacuum filtration
customLC/MS [5.51 min; 445 (M+1)]

Sources & evidence

ORD record: ord-c2f301cd9a8b4dbe9078b54fa4d117f8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802703B2

Reaction notes

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