3-Isoxazolamine → HCID 57898054, compound

HRID 1693574Notes

Reaction equation

HRID 1693574 reaction equation
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:9](=[O:25])[C:10]3[N:11]=[CH:12][N:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19](O)=[O:20])[C:14]=3[N:15]=2)=[CH:3][CH:2]=1.[NH2:39][C:40]1[CH:44]=[CH:43][O:42][N:41]=1>O=S(Cl)Cl>[C:1]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:9](=[O:25])[C:10]3[N:11]=[CH:12][N:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([NH:39][C:40]4[CH:44]=[CH:43][O:42][N:41]=4)=[O:20])[C:14]=3[N:15]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 18102163-IsoxazolamineHCID 57897855HCID 57897855, compound

Product 1

HCID 57898054HCID 57898054, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzoic acid (50 mg, 0.096 mmol) in SOCl2 (1 mL) was heated at 70° C. for 1 h. The reaction mixture was concentrated, dissolved in CH2Cl2 (2 mL), and treated with 3-aminoisoxazole (2.97 mg, 0.035 mmol). The reaction mixture was stirred at room temperature for 1 h, concentrated, and purified by flash column chromatography (silica gel, 0 30% Hex/EtOAc) to give the title compound 3-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-N-isoxazol-3-yl-benzamide as a white solid. 1H NMR (CDCl3□ (ppm) 9.94 (s, 1H), 8.46 (s, 1H), 8.32 (s, 1H), 8.29 (s, 1H), 8.08 (d, 1H), 8.02 (d, 1H), 7.72 (t, 1H), 7.49 (d, 2H), 7.45 (d, 2H), 7.39 (t, 2H), 7.35 7.29 (m, 5H), 7.25 (br s, 1H), 7.14 (d, 2H); HPLC-MS calculated for C30H20ClN5O2 (M+H+): 585.1. Found: 585.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in CH2Cl2 (2 mL)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (silica gel, 0 30% Hex/EtOAc)

Sources & evidence

ORD record
ord-6a9e5bb4b9b54fc089cbf73bc1a1aada
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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