Ethyl Acetate → HCID 178463377, compound

HRID 241062Notes

Reaction equation

HRID 241062 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[N:10]([CH2:13][CH3:14])=[C:11]=S.C(N=C=NC(C)C)(C)C.C(OCC)(=O)C>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:11]([NH:10][CH2:13][CH3:14])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10966Ethyl isothiocyanateHCID 12734DiisopropylcarbodiimideHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 178463377HCID 178463377, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
65 °C

Procedure

To a cooled (0° C.) solution of 5-bromopyridine-2,3-diamine (5.0 g, 27 mmol) in NMP (20 mL) was added isothiocyanatoethane (2.3 mL, 26 mmol). The resulting solution was heated (65° C.) for four hours and then cooled to ambient temperature before 1,3-diisopropylcarbodiimide (4.2 mL, 27 mmol) was added. The reaction mixture was stirred for 18 hours, diluted with water and the resulting suspension was collected by filtration. Trituration with ethyl acetate provided 6-bromo-N-ethyl-3H-imidazo[4,5-b]pyridin-2-amine (4.8 g, 75% yield) as a brown solid. 1H NMR (400 MHz, d6-DMSO) δ 11.41 (bs, 1H), 7.91 (s, 1H), 7.53 (s, 1H), 7.17 (s, 1H), 3.33 (q, 2H), 1.17 (t, 3H); MS (ES) for C8H9BrN4: 241 (MH+).

Workup

  1. additionwas added
  2. filtrationthe resulting suspension was collected by filtration

Sources & evidence

ORD record
ord-95f59e246c7c4f9b95b75e12dc17ecc1
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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