Ammonium Hydroxide → HCID 57897961, compound

HRID 1693570Notes

Reaction equation

HRID 1693570 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]([OH:21])=O)[C:14]=3[N:15]=2)=[CH:3][CH:2]=1.[NH4+:39].[OH-]>O=S(Cl)Cl.O>[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]([NH2:39])=[O:21])[C:14]=3[N:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 57897855HCID 57897855, compound

Product 1

HCID 57897961HCID 57897961, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 (40 mg, 0.077 mmol) in SOCl2 (1 mL) was heated at 70° C. for 1 h. The reaction mixture was allowed to cool to room temperature and poured into a 50% aqueous solution of NH4OH (15 mL). The resulting mixture was diluted with H2O and extracted with CH2Cl2. The combined organics were dried (MgSO4), filtered, and concentrated. The crude material was purified by flash column chromatography (silica gel, 5% MeOH/CH2Cl2) to give the title compound 3-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzamide as a white solid. 1H NMR (CDCl3) δ (ppm) 8.67 (s, 1H), 8.29 (t, 1H), 8.15 (br s, 1H), 8.02 (d, 1H), 7.98 (d, 1H), 7.71 (t, 1H), 7.64 (d, 2H), 7.58 (d, 3H), 7.46 (br s, 2H), 7.44 (m, 6H), 7.37 (m, 1H); HPLC-MS calculated for C30H20ClN5O2 (M+H+): 518.1. Found 518.1.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash column chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c406b4e70e8a4bba845402cd43a33284
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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