1,1'-Carbonyldiimidazole → HCID 71280455, compound

HRID 1497914Notes

Reaction equation

F[C:2]1([F:9])[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:23]=[C:24]([C:26]1[CH:27]=[CH:28][C:29]([CH3:44])=[C:30]([NH:32][C:33]([C:35]2[N:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]3=[N:37][CH:36]=2)=[O:34])[CH:31]=1)[NH2:25]>CN1C(=O)CCC1>[F:9][CH:2]1[CH2:3][CH:4]([C:6]2[O:8][N:23]=[C:24]([C:26]3[CH:27]=[CH:28][C:29]([CH3:44])=[C:30]([NH:32][C:33]([C:35]4[N:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]5=[N:37][CH:36]=4)=[O:34])[CH:31]=3)[N:25]=2)[CH2:5]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of 3,3-difluorocyclobutanecarboxylic acid (264 mg, 1.94 mmol) in anhydrous NMP (6 mL) was added 1,1′-carbonyldiimidazole (315 mg, 1.94 mmol). The reaction was stirred for 5 minutes. 5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (500 mg, 1.62 mmol) was added and the reaction was stirred for 25 minutes, then heated in the microwave at 120° C. for 12 minutes. The crude product was purified by silica chromatography to give N-(5-(5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F13). 1H NMR (400 MHz, d6-DMSO) δ 10.19 (s, 1H), 9.53-9.50 (m, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.90-7.87 (m, 1H), 7.83 (d, J=1.6, 8.0 Hz, 1H), 7.70-7.65 (m, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.33-7.29 (m, 1H), 3.93-3.84 (m, 1H), 3.25-3.02 (m, 4H), 2.37 (s, 3H). MS m/z 410.3 (M+1)+.

Workup

stirringthe reaction was stirred for 25 minutes
customThe crude product was purified by silica chromatography

Sources & evidence

ORD record: ord-8d024d7f962b4efb9fc7be0dd7cc4c2f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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