Diisopropylethylamine → 2-{3-[(5-Cyanopyridin-2-yl)amino]piperidin-1-yl}-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile

HRID 1183008Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:3]=1.Cl.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([NH:25][C:26]2[N:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[CH2:20]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([NH:25][CH:21]2[CH2:22][CH2:23][CH2:24][N:19]([C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([C:10]4[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=4[Cl:17])[N:3]=3)[CH2:20]2)=[N:31][CH:30]=1)#[N:33]

Participants

Conditions

Temperature: 120 °C

Procedure

60 mg (0.21 mmol) of 2-chloro-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile, 63 mg (0.25 mmol) of 6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride (Example 10A) and 0.184 ml (1.06 mmol) of N,N-diisopropylethylamine were initially charged in 2 ml of DMSO. The mixture was heated at 120° C. in a microwave for 30 min. The crude product was purified by means of preparative HPLC (method 13). 61 mg (64% of theory) of the product were obtained in solid form.

Workup

customThe crude product was purified by means of preparative HPLC (method 13)
custom61 mg (64% of theory) of the product were obtained in solid form

Sources & evidence

ORD record: ord-829bdce97628458793383c035ba87fad
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664246B2

Reaction notes

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