Acetyl chloride → 1-Acetyl-5-amino-7-chloro-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyrimidin-1-ium chloride

HRID 7520

Reaction equation

HRID 7520 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.[CH:10]1([N+:16]#[C-:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH:18](=O)[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.[C:25](Cl)(=[O:27])[CH3:26]>Cl(O)(=O)(=O)=O>[Cl-:8].[C:25]([N+:1]1[C:18]([C:19]2[O:23][CH:22]=[CH:21][CH:20]=2)=[C:17]([NH:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]2[C:4]([NH2:9])=[CH:5][C:6]([Cl:8])=[N:7][C:2]=12)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7362FurfuralHCID 674322,4-Diamino-6-chloropyrimidineHCID 79129Cyclohexyl isocyanide

Product 1

HCID 1784190021-Acetyl-5-amino-7-chloro-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyrimidin-1-ium chloride

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidSolvent

Procedure

Example 14 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloropyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) furfural solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.

Sources & evidence

ORD record
ord-6c88361f1cc54467bfce9e050513d95e
Source dataset
uspto-grants-2006_08
Patent number
US07087607B2

Linked notes

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