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

HRID 500515Notes

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-ce2a38a3a16f45178315a8f1aeb33090
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772233B2

Reaction notes

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