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

HRID 1183004Notes

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]([F:16])=[CH:12][CH:11]=2)[N:3]=1.Cl.[NH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([NH:24][C:25]2[N:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=2)[CH2:19]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[C:31]([C:28]1[CH:27]=[CH:26][C:25]([NH:24][CH:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([C:10]4[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=4)[N:3]=3)[CH2:19]2)=[N:30][CH:29]=1)#[N:32]

Participants

Conditions

Temperature: 120 °C

Procedure

60 mg (0.26 mmol) of 2-chloro-6-(4-fluorophenyl)pyridine-3-carbonitrile, 77 mg (0.31 mmol) of 6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride (Example 10A) and 0.225 ml (1.29 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). 99 mg (50% of theory) of the product were obtained in solid form.

Workup

customThe crude product was purified by means of preparative HPLC (method 13)
custom99 mg (50% of theory) of the product were obtained in solid form

Sources & evidence

ORD record: ord-c89d0a60f3014e5ba825a8082172c38e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664246B2

Reaction notes

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