1,1'-Carbonyldiimidazole → HCID 58026382, compound

HRID 1910128Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[NH:16][C:15]([NH2:18])=[N:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8].N1([C:24]([N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)=[O:25])C=CN=C1.C1C2[C:35](=[CH:36][CH:37]=[CH:38]C=2)[CH:34]=[C:33](N)N=1>CN(C=O)C>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[N:16]=[C:15]([NH:18][C:24]([NH:26][C:27]3[N:28]=[CH:29][C:30]4[C:37]([CH:38]=3)=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:25])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 48.4 mg (0.2 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) in dry DMF (1.0 mL) was added 49 mg (0.3 mmol) of di-imidazol-1-yl-methanone in one portion. The mixture was heated at 50° C. for 30 min, after cooling to room temperature, 23 mg (0.16 mmol) of isoquinolin-3-ylamine was added to the reaction mixtures. The reaction mixture was stirred at 45° C. for 45 min. After cooling to r.t., the organic solvent was removed under reduced pressure. The residue was purified by column chromatography eluting with DCM/methanol (v/v=10:1 to 8:1) to give 17 mg (20%) of 2-(3-isoquinolin-3-yl-ureido)-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. LCMS: 413 (M+1)+.

Workup

temperatureafter cooling to room temperature
temperatureAfter cooling to r.t.
customthe organic solvent was removed under reduced pressure
customThe residue was purified by column chromatography
washeluting with DCM/methanol (v/v=10:1 to 8:1)

Sources & evidence

ORD record: ord-815906cce55943d094aa084d59d68afc
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598353B2

Reaction notes

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