Methylamine → HCID 178486298, compound

HRID 1845776Notes

Reaction equation

HRID 1845776 reaction equation
[S:1]([NH2:5])(N)(=[O:3])=[O:2].[CH3:6]N.[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH2:15][CH2:16][C:17]1[C:18]([C:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=3)C(=O)[O:24][N:23]=2)=[N:19][O:20][N:21]=1.[OH-].[Na+]>N1C=CC=CC=1.O>[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:34][C:29]1[CH:28]=[C:27]([NH:26][C:22]([C:18]2[C:17]([CH2:16][NH:15][S:1]([NH:5][CH3:6])(=[O:3])=[O:2])=[N:21][O:20][N:19]=2)=[N:23][OH:24])[CH:32]=[CH:31][C:30]=1[F:33]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 82267SulfamideHCID 69266958HCID 69266958, compound

Product 1

HCID 178486298HCID 178486298, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

Sulfamide (32 mg, 0.33 mmol) and methylamine (15 μL, 0.33 mmol) were dissolved in pyridine (1.0 mL). The solution was heated to 120° C. for 5 minutes in a microwave. 3-[4-(aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate (32 mg, 0.075 mmol) was than added and the solution was heated to 120° C. for 3 minutes. A solution of sodium hydroxide in water (1 mL, 1 N) was added and the solution stirred at room temperature for 30 minutes. Acidification with acetic acid and purification by preparative LCMS gave the desired product (2.3 mg, 7%). MF=C11H12ClFN6O4S; LCMS calculated for C11H13ClFN6O4S (M+H)+: m/z=378.9.

Workup

  1. additionthan added
  2. temperaturethe solution was heated to 120° C. for 3 minutes
  3. customAcidification with acetic acid and purification by preparative LCMS

Sources & evidence

ORD record
ord-81cd6ace47994517aa335107124d04c0
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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