Potassium Carbonate → HCID 86621959, compound

HRID 77703Notes

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:13]=[CH:12][C:11]([CH3:14])=[C:10]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]4[CH:27]=[N:26][CH:25]=[N:24][C:20]=4[NH:21]3)=[CH:17][CH:16]=2)[CH:9]=1)=[O:6].[NH:35]1[CH:39]=[C:38]([CH:40]=[O:41])[N:37]=[CH:36]1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+]>CN(C=O)C.C1COCC1>[F:32][C:31]([F:34])([F:33])[C:42]([OH:43])=[O:45].[CH:40]([C:38]1[N:37]=[CH:36][N:35]([C:2]2[CH:3]=[C:4]([CH:28]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:30]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([C:15]3[CH:23]=[C:22]4[C:18]([C:19]5[CH:27]=[N:26][CH:25]=[N:24][C:20]=5[NH:21]4)=[CH:17][CH:16]=3)[CH:9]=2)=[O:6])[CH:39]=1)=[O:41]

Participants

Conditions

Temperature: 120 °C

Procedure

3-Fluoro-N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-5-(trifluoromethyl)-benzamide (0.030 g, 0.064 mmol) was mixed with 1H-imidazole-4-carbaldehyde (0.031 g, 0.32 mmol) and potassium carbonate (0.045 g, 0.32 mol) in DMF (0.7 mL) and was heated at 120° C. for 16 hours. The reaction was then diluted with THF and was filtered and the filtrate was concentrated in vacuo. The residue was purified by prep. LC to give the product (14 mg, 33% yield). 1H NMR (DMSO-d6): □ δ 13.13 (brs, 1H), 10.57 (s, 1H), 9.84 (s, 1H), 9.67 (s, 1H), 9.16 (s, 1H), 8.88 (d, 1H), 8.71 (d, 1H), 8.62 (m, 1H), 8.44 (m, 1H), 8.40 (d, 1H), 8.29 (m, 1H), 7.75 (m, 2H), 7.58 (s, 1H), 7.47 (m, 1H), 7.39 (m, 1H), 2.27 (s, 3H). MS (EI) m/z=541 (M+H).

Workup

filtrationwas filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by prep

Sources & evidence

ORD record: ord-8463660efeb0485facf94b23cccc7636
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841318B2

Reaction notes

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