Thieno(2,3-b)pyridine-2-carbaldehyde → HCID 178420753, compound

HRID 877302Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=4)=[CH:15][C:9]=3[N:8]=2)=[CH:3][CH:2]=1.[S:24]1[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=[C:25]1[CH:33]=O>CC(O)C.O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]5[NH:22][C:33]([C:25]6[S:24][C:28]7=[N:29][CH:30]=[CH:31][CH:32]=[C:27]7[CH:26]=6)=[N:23][C:18]=5[CH:17]=4)=[CH:15][C:9]=3[N:8]=2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 4-(2-(Pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine (intermediate A) (50 mg, 0.17 mmol), thieno[2,3-b]pyridine-2-carbaldehyde (33 mg, 0.20 mmol) and Na2S2O5 (38 mg. 0.20 mmol) in IPA-H2O (3:1, 8 mL) was heated under microwave radiation for 170° C. for 10 min. The mixture was absorbed onto silica and purified by column chromatography eluting with (95:5 EtOAc-MeOH to 85:15 EtOAc-MeOH) afforded the title compound as a yellow solid (30 mg, 0.07 mmol, 40%).

Workup

customThe mixture was absorbed onto silica
custompurified by column chromatography
washeluting with (95:5 EtOAc-MeOH to 85:15 EtOAc-MeOH)

Sources & evidence

ORD record: ord-5fe79f693afe45f78a2eafcc34d54a6d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987308B2

Reaction notes

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