1,1'-Carbonyldiimidazole → HCID 52915192, compound

HRID 1183533Notes

Reaction equation

[CH2:1]([C:8]1[N:13]=[C:12]([NH:14][C:15]2[C:16]([CH3:38])=[N:17][O:18][C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4([C:35](O)=[O:36])[CH2:34][CH2:33]4)=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:51][S:52]([NH2:55])(=[O:54])=[O:53].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:1]([C:8]1[N:13]=[C:12]([NH:14][C:15]2[C:16]([CH3:38])=[N:17][O:18][C:19]=2[C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4([C:35]([NH:55][S:52]([CH3:51])(=[O:54])=[O:53])=[O:36])[CH2:34][CH2:33]4)=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-{4′-[4-(6-benzyl-pyridin-2-ylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (sodium salt; 0.050 g, 0.083 mmol), carbonyldiimidazole (0.0676 g, 0.417 mmol), MeSO2NH2 (0.0789 g, 0.83 mmol) and DBU (0.0248 mL, 0.166 mmol) were combined in THF (1 mL) and the mixture was heated to 70° C. in a capped vial for 25 hours. The mixture was purified by preparative HPLC to yield the title compound.

Workup

customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-287ff55ec9f240d28c78afb588387016
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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