Methanol → HCID 178434787, compound

HRID 1639575Notes

Reaction equation

HRID 1639575 reaction equation
[C:1]1([NH:7][C:8](=[O:23])[CH:9]([C:17]2[S:21][N:20]=[C:19]([CH3:22])[N:18]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH2:26].[NH2:27]O.O>>[C:1]1([NH:7][C:8](=[O:23])[CH:9]([C:17]2[S:21][N:20]=[C:19]([CH3:22])[N:18]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[NH:27])[NH:16][OH:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 22235265Hydroxylamine monohydrateHCID 593780587-Cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid phenylamide

Product 1

HCID 178434787HCID 178434787, compound

Procedure

To a stirred mixture of 7-cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid phenylamide (2021044) (440 mg, 1.30 mmol) in 50% hydroxylamine/water (20 mL) was added methanol until the oil dissolved. The solution was then heated at reflux overnight. Water (100 mL) was added and the reaction mixture was then extracted with ethyl acetate (3×150 mL). The combined organic fractions were dried (MgSO4) and the solvent was removed under reduced pressure. The crude product (400 mg, 1.1 mmol) was purified by preparative liquid chromatography to afford 7-(N-hydroxycarbamimidoyl)-2-(3-methyl-[1,2,4]thiadiazol-5-yl)-heptanoic acid phenylamide (2021035) as a white solid.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution was then heated
  3. temperatureat reflux overnight
  4. extractionthe reaction mixture was then extracted with ethyl acetate (3×150 mL)
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a01ec2e11f9b46d1b5adad909e8c5b13
Source dataset
uspto-grants-2012_02
Patent number
US08110577B2

Reaction notes

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