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

HRID 2088708Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH:18]4[CH2:20][CH2:19]4)[CH2:13][CH2:12]3)[N:10]=[C:6]2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:3]=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([CH2:17][N:14]2[CH2:13][CH2:12][CH:11]([C:9]3[N:10]=[C:6]4[N:7]([C:2]([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:3][C:4]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])=[CH:5]4)[N:8]=3)[CH2:16][CH2:15]2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 130 °C

Procedure

50 mg (0.10 mmol) of 5-chloro-2-[1-(cyclopropylmethyl)piperidin-4-yl]-7-(2,4-dichlorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidine (Example 47A), 25 mg (0.12 mmol) of 6-[(2-aminoethyl)amino]-pyridin-3-carbonitrile hydrochloride (Example 2A) and 0.110 ml (0.6 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), 22 mg (38% of theory) of the product as a solid.

Workup

customThis gave, after purification of the crude product by preparative HPLC (Method 11), 22 mg (38% of theory) of the product as a solid

Sources & evidence

ORD record: ord-3f37d99a412a4efa967a042fba1b6781
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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