Isoxazole-5-carbonyl chloride → HCID 178522175, compound

HRID 555910Notes

Reaction equation

HRID 555910 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[C:6]([CH:8]=1)[NH2:7].[O:14]1[C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=[N:15]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[C:6]([NH:7][C:19]([C:18]2[O:14][N:15]=[CH:16][CH:17]=2)=[O:20])[CH:8]=1

Participants

3

Reactant 2

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 178507674HCID 178507674, compound

Product 1

HCID 178522175HCID 178522175, compoundYield 21%

Procedure

The title compound was prepared essentially according to the method of Example 4, but using 5-Chloro-2-(1H-tetrazol-5-yl)aniline (1.0 mmol) and isoxazole-5-carbonyl chloride. After precipitation the product was further purified by reverse phase C18 preparative HPLC (water/acetonitrile containing 0.1% formic acid 30%-100% gradient) to yield the desired product (61.1 mg, 21%). 1H NMR (400 MHz, d6-DMSO): δ 11.90 (s, 1H), 8.90 (s, 1H), 8.52 (s, 1H), 8.06 (d, 1H), 7.96 (s, 1H), 7.56 (dd, 1H), 7.30 (s, 1H). MS (EI) for C11H7ClN6O2: 290.7 (M+H).

Workup

  1. customThe title compound was prepared essentially
  2. customAfter precipitation the product
  3. customwas further purified by reverse phase C18 preparative HPLC (water/acetonitrile containing 0.1% formic acid 30%-100% gradient)

Sources & evidence

ORD record
ord-a7b6174f76374252a899488c0cc585e2
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

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