1,1'-Carbonyldiimidazole → HCID 71280455, compound

HRID 1497918Notes

Reaction equation

[F:1][CH:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:22]=[C:23]([C:25]1[CH:26]=[CH:27][C:28]([CH3:43])=[C:29]([NH:31][C:32]([C:34]2[N:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]3=[N:36][CH:35]=2)=[O:33])[CH:30]=1)[NH2:24]>CN1C(=O)CCC1>[F:1][CH:2]1[CH2:3][CH:4]([C:6]2[O:8][N:22]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([CH3:43])=[C:29]([NH:31][C:32]([C:34]4[N:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]5=[N:36][CH:35]=4)=[O:33])[CH:30]=3)[N:24]=2)[CH2:5]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of 3-fluorocyclobutanecarboxylic acid (76 mg, 0.647 mmol) in anhydrous NMP (1.5 mL) was added 1,1′-carbonyldiimidazole (105 mg, 0.647 mmol). The reaction was stirred for 5 minutes. 5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (100 mg, 0.323 mmol) was added and the reaction was stirred for 25 minutes, then heated in the microwave at 120° C. for 10 minutes. The crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F36). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.53-9.50 (m, 1H), 8.69 (s, 1H), 8.07 (d, J=1.6 Hz, 1H), 7.89-7.86 (m, 1H), 7.84 (dd, J=1.6, 8.0 Hz, 1H), 7.70-7.65 (m, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.32-7.29 (m, 1H), 5.48-5.28 (m, 1H), 3.99-3.91 (m, 1H), 2.81-2.73 (m, 4H), 2.37 (s, 3H). MS m/z 392.14 (M+1)+.

Workup

stirringthe reaction was stirred for 25 minutes
customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-49897d50704d4d7aa9382e90b0234f9b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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