1,1'-Carbonyldiimidazole → HCID 73407442, compound

HRID 1443489Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:22][CH:23]3[CH2:40][CH:39]4[CH:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42](O)=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)=[N:8][C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C1CCN2C(=NCCC2)CC1.[CH:70]1([S:73]([NH2:76])(=[O:75])=[O:74])[CH2:72][CH2:71]1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:22][CH:23]3[CH2:40][CH:39]4[CH:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42]([NH:76][S:73]([CH:70]6[CH2:72][CH2:71]6)(=[O:75])=[O:74])=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)=[N:8][C:9]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The acid 137 (130 mg, 0.207 mmol) and N,N,-carbonyldiimidazole (43 mg, 0.26 mmol) in THF (7 mL) were heated to reflux for 2 hours. DBU (29 μl), and cyclopropanesulfonamide, prepared as described in WO03/053349, (28 mg, 0.23 mmol) was then added and the mixture was stirred at 60° C. over-night. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with 0.5 M citric acid. Purification by HPLC gave 30 mg of the title compound. MS (M+H)+ 732.

Workup

temperatureto reflux for 2 hours
additionwas then added
washwashed with 0.5 M citric acid
customPurification by HPLC

Sources & evidence

ORD record: ord-eb3906554d8f4194bf37ab2596e27d70
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659245B2

Reaction notes

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