1,1'-Carbonyldiimidazole → HCID 16214898, compound

HRID 2039669Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13].[CH3:24][NH:25][C:26]([C:28]1[CH:33]=[C:32]([O:34][C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[C:37]([F:42])[CH:36]=2)[CH:31]=[CH:30][N:29]=1)=[O:27]>ClC(Cl)C>[CH3:24][NH:25][C:26]([C:28]1[CH:33]=[C:32]([O:34][C:35]2[CH:40]=[CH:39][C:38]([NH:41][C:12]([NH:1][C:2]3[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[N:5]=[CH:4][N:3]=3)=[O:13])=[C:37]([F:42])[CH:36]=2)[CH:31]=[CH:30][N:29]=1)=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 8-mL screw-cap vial, 4-amino-6-trifluoromethylpyrimidine (170 mg, 1.04 mmol) was added to a slurry of 1,1′-carbonyldiimidazole (169 mg, 1.04 mmol) in dichloroethane (0.35 mL). The mixture was heated at 60° C. for 30 hours. 4-(4Amino-3-fluoro-phenoxy)-pyridine-2-carboxylic acid methylamide (170 mg, 1.04 mmol) was then added and the mixture was heated overnight at to 60° C. The solvent was evaporated under reduced pressure, and the solid residue was washed with methanol to give the title product as a white solid (139 mg, yield 30%). 1H NMR (400 MHz, DMSO-d6) δ 10.6 (s, 1 H), 9.7 (s, 1 H), 9.0 (s, 1 H), 8.8 (s, 1 H), 8.5 (d, 1 H), 8.20 (m, 2 H), 7.40 (m, 2 H), 7.18 (d, 1 H), 7.10 (d, 1 H), 2.80 (s, 3 H). LC-MS m/z 451.3 [M+H]+.

Workup

customIn a 8-mL screw-cap vial
temperaturethe mixture was heated overnight at to 60° C
customThe solvent was evaporated under reduced pressure
washthe solid residue was washed with methanol

Sources & evidence

ORD record: ord-f77e03b7c13844739aba2ca507a729cf
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580798B2

Reaction notes

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