Citric Acid → HCID 89815259, compound

HRID 2172299Notes

Reaction equation

HRID 2172299 reaction equation
[S:1]1[C:5]([NH2:6])=[N:4][CH:3]=[N:2]1.C(N(CC)CC)C.[S:14](Cl)(Cl)(=[O:16])=[O:15].Cl.[Cl:20][C:21]1[N:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][NH:25][CH2:26]2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[Cl:20][C:21]1[N:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][N:25]([S:14]([NH:6][C:5]1[S:1][N:2]=[CH:3][N:4]=1)(=[O:16])=[O:15])[CH2:26]2

Participants

7

Reactant 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 2902745-Amino-1,2,4-thiadiazoleHCID 898134595-chloro-1,2,3,4-tetrahydro-2,6-naphthyridine hydrochloride

Product 1

HCID 89815259HCID 89815259, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,4-thiadiazol-5-amine (0.740 g, 7.31 mmol) and triethylamine (3.06 ml, 21.94 mmol) in 20 mL DCM was cooled to −78° C. and was treated with sulfuryl chloride (0.595 ml, 7.31 mmol). The cooling bath was removed, and the reaction mixture was allowed to stir for 20 minutes. LC/MS showed mostly desired intermediate, so 5-chloro-1,2,3,4-tetrahydro-2,6-naphthyridine hydrochloride (Anichem, North Brunswick, N.J., 0.750 g, 3.66 mmol) was added and the reaction mixture was allowed to stir for one hour. The reaction mixture was then poured into 1N citric acid and was extracted with EtOAc. The organics were concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-chloro-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2,6-naphthyridine-2(1H)-sulfonamide (1.064 g, 3.21 mmol). [M+H]+=332.1

Workup

  1. customThe cooling bath was removed
  2. additionwas added
  3. stirringto stir for one hour
  4. extractionwas extracted with EtOAc
  5. concentrationThe organics were concentrated
  6. customPurification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-a8460d65f636487bbc7434c7f61ca17f
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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