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

HRID 2088705Notes

Reaction equation

Cl.Cl[C:3]1[N:8]2[N:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15]([CH:18]4[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[N:11]=[C:7]2[CH:6]=[C:5]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:4]=1.Cl.Cl.[NH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][N:36]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH:18]1([N:15]2[CH2:16][CH2:17][CH:12]([C:10]3[N:11]=[C:7]4[N:8]([C:3]([NH:31][CH2:32][CH2:33][NH:34][C:35]5[N:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=5)=[N:4][C:5]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])=[CH:6]4)[N:9]=3)[CH2:13][CH2:14]2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 130 °C

Procedure

21 mg (0.10 mmol) of 5-chloro-7-(2,4-dichlorophenyl)-2-(1-cyclopropylpiperidin-4-yl)[1,2,4]-triazolo[1,5-c]pyrimidine hydrochloride (Example 45A), 40 mg (0.10 mmol) of 6-[(2-aminoethyl)-amino]pyridin-3-carbonitrile hydrochloride (Example 2A) and 0.10 ml (0.57 mmol) of N,N-diisopropylethylamine were initially charged in 1 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), 32 mg (62% of theory) of the product as a solid.

Workup

customThis gave, after purification of the crude product by preparative HPLC (Method 11), 32 mg (62% of theory) of the product as a solid

Sources & evidence

ORD record: ord-e4805cab33a84c12a7308c2f79d3743a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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