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

HRID 1183006Notes

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.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[C:21]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)[N:20]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[C:21]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][N:30]([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)[CH2:29]2)[N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

55 mg (0.24 mmol) of 2-chloro-6-(4-fluorophenyl)pyridine-3-carbonitrile, 74 mg (0.28 mmol) of 2-amino-6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride (Example 11A) and 0.206 ml (1.18 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). 47 mg (48% of theory) of the product were obtained in solid form.

Workup

customThe crude product was purified by means of preparative HPLC (method 13)
custom47 mg (48% of theory) of the product were obtained in solid form

Sources & evidence

ORD record: ord-040e1df37bff4f939b9ca97d43413b76
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664246B2

Reaction notes

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