Ethanol → HCID 21196274, compound

HRID 1108248Notes

Reaction equation

HRID 1108248 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 title 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-5905590d114344df82c850215802f094
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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