Hydrochloric Acid → 4-Amino-2-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]-1,3-thiazole-5-carbonitrile

HRID 2389825Notes

Reaction equation

Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.FC(F)(F)C(O)=O.[NH2:26][C:27]1[N:28]=[C:29]([NH:34][CH2:35][CH2:36][NH2:37])[S:30][C:31]=1[C:32]#[N:33].CCN(C(C)C)C(C)C.Cl>O.CS(C)=O>[NH2:26][C:27]1[N:28]=[C:29]([NH:34][CH2:35][CH2:36][NH:37][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])[N:3]=2)[S:30][C:31]=1[C:32]#[N:33]

Participants

Conditions

Temperature: 120 °C

Procedure

214.27 mg (0.72 mmol) of chloropyrimidine (Example 6A) are introduced into 28 ml of dry DMSO, 320 mg (1.08 mmol) of 4-amino-2-[(2-aminoethyl)amino]-1,3-thiazole-5-carbonitrile trifluoroacetate (Example 20A) and 742 mg (5.74 mmol) of DIPEA are added, and the mixture is heated at 120° C. under argon for 16 h. Water is added, and the mixture is neutralized with 1N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are freed of solvent, and the residue is purified by preparative HPLC. 48.4 mg (14% of theory) of the product are obtained as a solid.

Workup

additionare added
extractionextracted three times with ethyl acetate
customthe residue is purified by preparative HPLC
custom48.4 mg (14% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-61332eb598214544bfce6b7e5be78ba7
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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