Isobutylamine → HCID 66659119, compound

HRID 420511Notes

Reaction equation

HRID 420511 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:18]=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9].[CH2:21]([NH2:25])[CH:22]([CH3:24])[CH3:23]>CCOC(C)=O>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:25][CH2:21][CH:22]([CH3:24])[CH3:23])[C:3]2[N:4]([CH:18]=[CH:19][N:20]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 66659136HCID 66659136, compound

Product 1

HCID 66659119HCID 66659119, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a sealed tube, a mixture of 8-chloro-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (20 mg, 0.062 mmol) and isobutylamine (0.037 mL, 0.37 mmol) was heated at 150° C. for 14 h. The reaction mixture was cooled to RT, poured into AcOEt (5 mL) and washed with a 2.0 M Na2CO3 solution in water (2×2 mL). The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→8:2) to yield the title compound (19.1 mg, 0.053 mmol, 85%) as a reddish solid. MS: 359 [M+1]+; HPLC: AtRet=2.61; TLC: RF 0.64 (hexane/DCM/TBME 1:1:2).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with a 2.0 M Na2CO3 solution in water (2×2 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→8:2)

Sources & evidence

ORD record
ord-b12b6e7b34a541c789c3060edbb071aa
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

Loading…