1,1'-Carbonyldiimidazole → HCID 59026838, compound

HRID 658405Notes

Reaction equation

C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:28]=[N:27][CH:26]=[C:25]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=2[F:37])[C:21]=1[C:22]([OH:24])=O.C([O-])(=O)C.[NH4+]>CS(C)=O>[F:37][C:31]1[CH:32]=[C:33]([I:36])[CH:34]=[CH:35][C:30]=1[NH:29][C:25]1[CH:26]=[N:27][CH:28]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[F:13])[C:21]=1[C:22]([NH2:3])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

1,1′-carbonyldiimidazole (70 mg, 0.43 mmol) was added to a solution of 3-(2-fluoro-phenyl)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinic acid (130 mg, 0.29 mmol) in DMSO (1 mL), and stirred overnight at 60° C. Ammonium acetate (89 mg, 1.15 mmol) was added, and the reaction solution was stirred for an additional 4 h at 60° C. The reaction solution was quenched with H2O, diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 70% EtOAc in hexanes to afford the desired product (78 mg, 60%). LC-MS (M+H=452, obsd.=452).

Workup

stirringthe reaction solution was stirred for an additional 4 h at 60° C
customThe reaction solution was quenched with H2O
additiondiluted with EtOAc
filtrationfiltered through an Extrelut column
washThe column was washed with EtOAc
concentrationthe filtrate was concentrated
customThe crude product was purified via Biotage
washeluting with a gradient of 0 to 70% EtOAc in hexanes

Sources & evidence

ORD record: ord-2c4603a2fbf34dba9c77d9147e546405
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076486B2

Reaction notes

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