Sodium Hydroxide → HCID 178514777, compound

HRID 2097646Notes

Reaction equation

HRID 2097646 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][C:10]1[C:11]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)C(=O)[O:17][N:16]=2)=[N:12][O:13][N:14]=1.[S:29](N)([NH2:32])(=[O:31])=[O:30].[OH-].[Na+]>N1C=CC=CC=1.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:32][S:29]([NH:8][CH2:9][C:10]1[C:11]([C:15](=[N:16][OH:17])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=2)=[N:12][O:13][N:14]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 82267SulfamideHCID 69266958HCID 69266958, compound

Product 1

HCID 178514777HCID 178514777, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

3-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate (30 mg, 0.07 mmol) and sulfamide (20 mg, 0.2 mmol) was dissolved in pyridine (1.0 mL) and heated at 120° C. for 3 min in a microwave. A solution of sodium hydroxide in water (0.5 mL, 1 N) was added and the solution was stirred for 30 minutes. Acidification with acetic acid and purification by preparative LCMS gave the desired product (17 mg, 50%). MF═C10H10ClFN6O4S; LCMS calculated for C10H11ClFN6O4S(M+H)+: m/z=364.9. 1H NMR (400 MHz, CD3OD): δ 7.02 (m, 2H), 6.76 (m, 1H), 4.50 (s, 2H).

Workup

  1. customAcidification with acetic acid and purification by preparative LCMS

Sources & evidence

ORD record
ord-867d6dcf1f5e4217a52a2cf8bb13ad58
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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