Imidazole → 3-(1H-imidazol-1-yl)-N-[6-methyl-5-(9H-pyrimido[4,5-b]indol-7-yl)pyridin-3-yl]-5-(trifluoromethyl)benzamide tris(trifluoroacetate)

HRID 77736Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([CH3:27])=[C:12]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]4[CH:26]=[N:25][CH:24]=[N:23][C:19]=4[NH:20]3)=[CH:16][CH:15]=2)[CH:13]=1)=[O:6].[NH:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.[C:40](=[O:43])([O-])[O-:41].[K+].[K+]>CN(C)C=O.C1COCC1>[F:32][C:31]([F:34])([F:33])[C:40]([OH:41])=[O:43].[F:32][C:31]([F:34])([F:33])[C:40]([OH:41])=[O:43].[F:32][C:31]([F:34])([F:33])[C:40]([OH:41])=[O:43].[N:35]1([C:2]2[CH:3]=[C:4]([CH:28]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:30]=2)[C:5]([NH:7][C:8]2[CH:9]=[N:10][C:11]([CH3:27])=[C:12]([C:14]3[CH:22]=[C:21]4[C:17]([C:18]5[CH:26]=[N:25][CH:24]=[N:23][C:19]=5[NH:20]4)=[CH:16][CH:15]=3)[CH:13]=2)=[O:6])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-fluoro-N-[6-methyl-5-(9H-pyrimido[4,5-b]indol-7-yl)pyridin-3-yl]-5-(trifluoromethyl)benzamide (0.023 g, 0.049 mmol) in N,N-dimethylformamide (0.50 mL) was added 1H-imidazole (0.016 g, 0.24 mmol) and potassium carbonate (0.034 g, 0.25 mmol) and was heated at 120° C. for 16 hours. The reaction was diluted with THF, was filtered, was rotovaped and was purified by preparative LC to give the product. 1H NMR (400 MHZ, DMSO-D6): δ 13.06 (brs, 1H), 10.99 (s, 1H), 9.65 (s, 1H), 9.54 (brs, 1H), 9.13 (s, 1H), 8.99 (d, 1H), 8.64 (s, 1H), 8.44 (m, 3H), 8.36 (s, 1H), 8.25 (d, 1H), 7.78 (s, 1H), 7.66 (s, 1H), 7.50 (m, 1H), 2.52 (s, 1H); MS (ES) (M+H)=514.

Workup

filtrationwas filtered
customwas purified by preparative LC
customto give the product

Sources & evidence

ORD record: ord-1d5a6700fb3347dd924412b58594418d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841318B2

Reaction notes

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