1,1'-Carbonyldiimidazole → HCID 71280624, compound

HRID 1497936Notes

Reaction equation

[O:1]=[C:2]1[CH2:11][C:4]2([CH2:7][CH:6]([C:8]([OH:10])=O)[CH2:5]2)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:25]=[C:26]([C:28]1[CH:29]=[CH:30][C:31]([CH3:46])=[C:32]([NH:34][C:35]([C:37]2[N:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]3=[N:39][CH:38]=2)=[O:36])[CH:33]=1)[NH2:27]>CN1C(=O)CCC1>[CH3:46][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[N:25]=[C:8]([CH:6]3[CH2:5][C:4]4([CH2:3][C:2](=[O:1])[CH2:11]4)[CH2:7]3)[O:10][N:27]=2)=[CH:33][C:32]=1[NH:34][C:35]([C:37]1[N:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]2=[N:39][CH:38]=1)=[O:36]

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of 6-oxospiro[3.3]heptane-2-carboxylic acid (50 mg, 0.32 mmol) in anhydrous NMP (1 mL) was added 1,1′-carbonyldiimidazole (CDI) (52.3 mg, 0.32 mmol). The reaction was stirred for 3 minutes. N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (100 mg, 0.32 mmol) was added and the reaction was stirred for 25 minutes. Then, the reaction was heated at 120° C. for 15 minutes. The crude reaction was purified by reverse phase preparative HPLC to give N-(2-methyl-5-(5-(6-oxospiro[3.3]heptan-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F75). MS m/z 428.2 (M+1)+.

Workup

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

Sources & evidence

ORD record: ord-fd6936c24fa44477947101a6ed179be9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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