Diisopropylethylamine → 1-[2-Amino-6-({1-[2-(1-cyclopropylpiperidin-4-yl)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]-pyrimidin-5-yl]piperidin-3-yl}amino)pyridin-3-yl]propan-1-one

HRID 2088706Notes

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.[NH2:30][C:31]1[C:36]([C:37](=[O:40])[CH2:38][CH3:39])=[CH:35][CH:34]=[C:33]([NH:41][CH:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)[N:32]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[NH2:30][C:31]1[C:36]([C:37](=[O:40])[CH2:38][CH3:39])=[CH:35][CH:34]=[C:33]([NH:41][CH:42]2[CH2:47][CH2:46][CH2:45][N:44]([C:3]3[N:8]4[N:9]=[C:10]([CH:12]5[CH2:17][CH2:16][N:15]([CH:18]6[CH2:19][CH2:20]6)[CH2:14][CH2:13]5)[N:11]=[C:7]4[CH:6]=[C:5]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[N:4]=3)[CH2:43]2)[N:32]=1

Participants

Conditions

Temperature: 120 °C

Procedure

25 mg (0.06 mmol) of 5-chloro-7-(2,4-dichlorophenyl)-2-(1-cyclopropylpiperidin-4-yl)-[1,2,4]-triazolo[1,5-c]pyrimidine hydrochloride, 20 mg (0.07 mmol) of 1-[2-amino-6-(piperidin-3-ylamino)pyridin-3-yl]propan-1-one hydrochloride (Example 27A) and 65 μl (0.4 mmol) of N,N-diisopropylethylamine were initially charged in 1.25 ml of DMSO. The mixture was heated in the microwave at 120° C. for 30 min. This gave, after purification of the crude product by preparative HPLC (Method 11), 21 mg (56% of theory) of the product as a solid.

Workup

customThis gave, after purification of the crude product by preparative HPLC (Method 11), 21 mg (56% of theory) of the product as a solid

Sources & evidence

ORD record: ord-510a0b27064c400888b31ee689de0d83
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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