Aminoacetonitrile sulfate (1:1) → HCID 178420611, compound

HRID 1093524Notes

Reaction equation

[N:1]([O-])=O.[Na+].[N:5]1[CH:6]=[C:7]([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)[N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12.S(O)(O)(=O)=O.[NH2:26][CH2:27][C:28]#[N:29].CC([O-])=O.[Na+]>O.Cl>[N:5]1[CH:6]=[C:7]([C:14]2[CH:15]=[C:16]([NH:20][C:28]3[NH:29][N:1]=[N:26][CH:27]=3)[CH:17]=[CH:18][CH:19]=2)[N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of sodium nitrite (140 mg, 2 mmol) in H2O (1 ml) was added to a stirred solution of 3-imidazo[1,2-a]pyridin-3-yl-phenylamine (420 mg, 2 mmol) in 2N HCl (4 ml) such that the internal temperature <5° C. After complete addition the reaction was stirred 15 minutes at this temperature before the addition of aminoacetonitrile hydrogen sulphate (310 mg, 2 mmol) in H2O (1 ml) [internal temperature maintained <5° C.]. After 1 hour NaOAc (7 g) was added. The mixture was stirred for 1 hour with ice bath cooling, then the solid was collected by filtration. This material was taken up in EtOH directly (˜10 ml). This solution was stirred and heated at 90° C. for 18 hours under N2. After cooling to RT the volatiles were removed in vacuo and the residue was purified by chromatography on silica (100% CH2Cl2→4% 2M NH3-MeOH/CH2Cl2) to give the title compound (219 mg, solid). MS: [M+H]+ 277

Workup

additionAfter complete addition the reaction
temperaturecooling
filtrationthe solid was collected by filtration
stirringThis solution was stirred
temperatureAfter cooling to RT the volatiles
customwere removed in vacuo
customthe residue was purified by chromatography on silica (100% CH2Cl2→4% 2M NH3-MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-388389cb21fa4dc3944b18f67d1977d7
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08131527B1

Reaction notes

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