Diisopropylethylamine → 1-(2-Amino-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}pyridin-3-yl)-2,2,2-trifluoroethanone

HRID 2088707Notes

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.[NH2:30][C:31]1[C:36]([C:37](=[O:42])[C:38]([F:41])([F:40])[F:39])=[CH:35][CH:34]=[C:33]([NH:43][CH2:44][CH2:45][NH2:46])[N:32]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[NH2:30][C:31]1[C:36]([C:37](=[O:42])[C:38]([F:39])([F:41])[F:40])=[CH:35][CH:34]=[C:33]([NH:43][CH2:44][CH2:45][NH:46][C:2]2[N:7]3[N:8]=[C:9]([CH:11]4[CH2:16][CH2:15][N:14]([CH2:17][CH:18]5[CH2:20][CH2:19]5)[CH2:13][CH2:12]4)[N:10]=[C:6]3[CH:5]=[C:4]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:3]=2)[N:32]=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), 35 mg (0.12 mmol) of 1-{2-amino-6-[(2-aminoethyl)amino]pyridin-3-yl}-2,2,2-trifluoroethanone hydrochloride (Example 13A) 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), 32 mg (48% of theory) of the product as a solid.

Workup

customThis gave, after purification of the crude product by preparative HPLC (Method 11), 32 mg (48% of theory) of the product as a solid

Sources & evidence

ORD record: ord-96812c84203044e88619ffaa3c67323b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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