Ammonia → HCID 22022996, compound

HRID 1793675Notes

Reaction equation

HRID 1793675 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH2:25][CH:24]([CH2:26][O:27][C:28]3[CH:32]=[CH:31][O:30][N:29]=3)[O:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:20])[CH2:15][O:16]C(=O)C)[CH2:10][CH2:9]1.N>CO.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH2:25][CH:24]([CH2:26][O:27][C:28]3[CH:32]=[CH:31][O:30][N:29]=3)[O:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:20])[CH2:15][OH:16])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 22022958HCID 22022958, compound

Product 1

HCID 22022996HCID 22022996, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5RS)-3-(3-Fluoro-4(4-(2-acetoxyacetyl)piperazin-1-yl)phenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (112 mg, 0.25 mM) was suspended in a saturated solution of ammonia in methanol (8 ml), diluted with tetrahydrofuran (5 ml). The mixture was stirred at ambient temperature for 40 hours. The residue after evaporation was chromatographed on a 5 g silica Mega Bond Elut® column, eluting with a gradient from 0–5% methanol in dichloromethane. Relevant fractions were combined to give the desired product (92 mg).

Workup

  1. customThe residue after evaporation
  2. customwas chromatographed on a 5 g silica Mega Bond Elut® column
  3. washeluting with a gradient from 0–5% methanol in dichloromethane

Sources & evidence

ORD record
ord-61c912b3d1694021932ca1ed5a83cc08
Source dataset
uspto-grants-2006_07
Patent number
US07081538B1

Reaction notes

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