Ethanol → HCID 21196274, compound

HRID 1066874Notes

Reaction equation

HRID 1066874 reaction equation
[CH2:1]([N:4]=[C:5]=[S:6])[CH2:2][CH3:3].C(N(CC)CC)C.Br.[NH2:15][C:16]1[C:21]([C:22]([OH:24])=O)=[CH:20][C:19]([Br:25])=[CH:18][N:17]=1.C(O)C>CN(C)C=O>[Br:25][C:19]1[CH:18]=[N:17][C:16]2[NH:15][C:5](=[S:6])[N:4]([CH2:1][CH2:2][CH3:3])[C:22](=[O:24])[C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 69403Propyl IsothiocyanateHCID 573505542-Amino-5-bromopyridine-3-carboxylic acid--hydrogen bromide (1/1)

Product 1

HCID 21196274HCID 21196274, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of n-propyl isothiocyanate (1.59 g, 1.62 mL), triethylamine (5.0 g, 13.8 mL), and 5.0 g of the tide compound of Step A was heated to 100-110° C. in 22 mL of dimethylformamide for 48 h. The reaction mixture was then allowed to cool to room temperature and treated with 10 mL of ethanol. The resulting precipitate was filtered, washed with ethanol followed by hexanes and dried to deliver 2.48 g of the title compound of Step B. 1H NMR (400 MHz, Me2SO-d6): δ 0.90 (t,3H), 1.60-1.78 (m,2H), 4.30 (t,2H), 8.41 (s,1H), 8.82 (s,1H), 13.55 (s,1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-09b4c2d49279414ca0e928787f4c4d06
Source dataset
uspto-grants-2001_06
Patent number
US06245770B1

Reaction notes

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