1,1'-Carbonyldiimidazole → HCID 71280386, compound

HRID 1497937Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of 2,2-difluorocyclopropanecarboxylic acid (325 mg, 2.66 mmol) in anhydrous NMP (7 mL) was added 1,1′-carbonyldiimidazole (CDI) (432 mg, 2.66 mmol). The reaction was stirred for 3 minutes. N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (825 mg, 2.66 mmol) was added and the reaction was stirred for 25 minutes. Then, the reaction was heated at 120° C. for minutes. The crude product was purified on silica gel using 10% MeOH in dichloromethane to give N-(5-(5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F64). 1H NMR (400 MHz, d6-DMSO) δ 9.60 (d, J=7.2 Hz, 1H), 8.56 (d, J=1.6 Hz, 1H), 8.51 (s, 1H), 8.12 (bs, 1H), 7.87 (dd, J=2.0, 7.8 Hz, 1H), 7.82 (d, J=9.2 Hz, 1H), 7.58-7.53 (m, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.16 (td, J=0.8, 6.8 Hz, 1H), 3.19-3.12 (m, 1H), 2.48 (s, 3H), 2.45-2.36 (m, 1H), 2.27-2.18 (m, 1H). MS m/z 396.1 (M+1)+.

Workup

stirringthe reaction was stirred for 25 minutes
customThe crude product was purified on silica gel using 10% MeOH in dichloromethane

Sources & evidence

ORD record: ord-8a75bf68a57d416c9e65fadc64c95fe8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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