3,4-Diaminopyridine → biphenyl-4-yl[4-(1H-imidazo[4,5-c]pyridin-2-yl)piperidin-1-yl]methanone

HRID 1913159

Reaction equation

[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15](O)=O)[CH2:11][CH2:10]2)=[O:8])=[CH:3][CH:2]=1.[NH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][C:30]=1[NH2:31].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>N1C=CC=CC=1>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[NH:31][C:30]4[CH:29]=[CH:28][N:27]=[CH:26][C:25]=4[N:24]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 1-(biphenyl-4-ylcarbonyl)piperidine-4-carboxylic acid (0.10 g, 0.32 mmol) and 3,4-diaminopyridine (35 mg, 0.32 mmol) in pyridine (1 mL) is added triphenyl phosphate (0.10 mL, 0.38 mmol). The mixture is heated under microwave irradiation at 120° C. for 50 mins. Purification by preparative HPLC gives 34 mg of biphenyl-4-yl[4-(1H-imidazo[4,5-c]pyridin-2-yl)piperidin-1-yl]methanone.

Workup

customPurification by preparative HPLC

Sources & evidence

ORD record: ord-372b6ab6863c4d32aaf284a40ee14b9c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609696B2

Linked notes

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