Ammonia → HCID 21293085, compound

HRID 622383Notes

Reaction equation

HRID 622383 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.CO[C:16]1[C:20](OC)=[N:19][S:18](=[O:23])[N:17]=1.[NH3:24]>CO>[NH2:24][C:16]1[C:20]([NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:5]2[C:4]([CH3:13])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[N:19][S:18](=[O:23])[N:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 14397364HCID 14397364, compound

Product 1

HCID 21293085HCID 21293085, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(5-Bromo-3-methylpyrid-2-ylamino)propylamine (0.713 g) was added dropwise to a stirred solution of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.639 g) in methanol (25 ml) at room temperature. After 4 hours at room temperature, methanolic ammonia (25 ml) was added at 0°-5° C. with stirring, the mixture allowed to stand overnight, then evaporated in vacuo. The residue was chromatographed on silica in 10% CH3OH/CHCl3. The product was crystallised from ethanol to give 4-amino-3-[3-(5-bromo-3-methylpyrid-2-ylamino)propylamino]-1,2,5-thiadiazole-1-oxide (0.322 g, 32%) m.p. 204°-205° C.

Workup

  1. waitto stand overnight
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on silica in 10% CH3OH/CHCl3
  4. customThe product was crystallised from ethanol

Sources & evidence

ORD record
ord-a2a459bc4dcd41118da6ba2c1c21e0b1
Source dataset
uspto-grants-1988_09
Patent number
US04771058

Reaction notes

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