Triethylamine → 4-Amino-2-({2-[(6-bromoimidazo[1,2-a]pyrazin-8-yl)amino]ethyl}amino)-1,3-thiazole-5-carbonitrile

HRID 57668

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

300 mg (1.08 mmol) of 6,8-dibromoimidazo[1,2-a]pyrazine were dissolved in 10 ml of DMSO, and 0.6 ml (4.3 mmol) of triethylamine and 360 mg (1.3 mmol) of 4-amino-2-[(2-aminoethyl)amino]-1,3-thiazole-5-carbonitrile dihydrochloride (Example 8A) were added. The mixture was heated at 140° C. in a microwave for 1 h. Purification by preparative HPLC gave 376 mg (83% of theory) of the product as a solid.

Workup

customPurification by preparative HPLC

Sources & evidence

ORD record: ord-5bfda0b3f3b64eefb76a883114688c89
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Linked notes

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