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

HRID 1183007Notes

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.[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:22]([NH:28][CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[N:21]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:22]([NH:28][CH:29]2[CH2:34][CH2:33][CH2:32][N:31]([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)[CH2:30]2)[N:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

55 mg (0.19 mmol) of 2-chloro-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile, 60.9 mg (0.23 mmol) of 2-amino-6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride (Example 11A) and 0.169 ml (0.97 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). 30 mg (33% of theory) of the product were obtained in solid form.

Workup

customThe crude product was purified by means of preparative HPLC (method 13)
custom30 mg (33% of theory) of the product were obtained in solid form

Sources & evidence

ORD record: ord-dd2ff3e8b4904712904b618c5cd22cf5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664246B2

Reaction notes

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