Diisopropylethylamine → 6-[(2-{[6-(2,4-Dichlorophenyl)imidazo[1,2-a]pyrazin-8-yl]amino}ethyl)amino]nicotinonitrile

HRID 57708Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([CH:16]=[CH:17][N:18]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:7]=1.Cl.Cl.[NH2:21][CH2:22][CH2:23][NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[Cl:15][C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([NH:21][CH2:22][CH2:23][NH:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=2)[C:3]2[N:4]([CH:16]=[CH:17][N:18]=2)[CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

108 mg (0.3625 mmol) of the 8-chloro-6-(2,4-dichlorophenyl)imidazo[1,2-a]pyrazine (Example 5A) were initially charged in 3 ml of DMSO, and 150 mg (0.543 mmol) of 6-[(2-aminoethyl)amino]nicotinonitrile (Example 2A) and 0.63 ml (3.62 mmol) of N,N-diisopropylethylamine were added. The mixture was heated at 120° C. for 12 h. Purification by chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 100:1) gave 12 mg (7% of theory) of the product.

Workup

customPurification by chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 100:1)
customgave 12 mg (7% of theory) of the product

Sources & evidence

ORD record: ord-f80bd55336564a189446e7e239e248ac
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Reaction notes

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