Diisopropylethylamine → 6-[(2-{[7-(2,4-Dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]-amino}ethyl)amino]pyridine-3-carbonitrile

HRID 2088712Notes

Reaction equation

Cl.Cl[C:3]1[N:8]2[N:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[N:11]=[C:7]2[CH:6]=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:4]=1.Cl.Cl.[NH2:29][CH2:30][CH2:31][NH:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][N:34]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:5]1[N:4]=[C:3]([NH:29][CH2:30][CH2:31][NH:32][C:33]2[N:34]=[CH:35][C:36]([C:37]#[N:38])=[CH:39][CH:40]=2)[N:8]2[N:9]=[C:10]([CH:12]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]3)[N:11]=[C:7]2[CH:6]=1

Participants

Conditions

Temperature: 130 °C

Procedure

50 mg (0.13 mmol) of 5-chloro-7-(2,4-dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo-[1,5-c]pyrimidine hydrochloride (Example 49A), 30 mg (0.15 mmol) of 6-[(2-aminoethyl)amino]pyridin-3-carbonitrile hydrochloride (Example 2A) and 0.13 ml (0.76 mmol) of N,N-diisopropylethylamine were initially charged in 1.5 ml of DMSO. The mixture was heated in the microwave at 130° C. for 30 min. This gave, after purification of the crude product by preparative HPLC (Method 11), 25 mg (37% of theory) of the product as a solid.

Workup

customThis gave, after purification of the crude product by preparative HPLC (Method 11), 25 mg (37% of theory) of the product as a solid

Sources & evidence

ORD record: ord-7b711339f85c49c5867d777422789ded
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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