HCID 67282126, compound → HCID 57897836, compound

HRID 1693572Notes

Reaction equation

HRID 1693572 reaction equation
[C:1]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)[C:9](=[O:37])[C:10]3[N:11]=[C:12]([CH2:22][N:23](CC4C=CC(OC)=CC=4)[S:24]([CH3:27])(=[O:26])=[O:25])[N:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3[N:15]=2)=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[C:1]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:2]=[CH:3][C:4]([C:7]2[N:8]([C:38]3[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=3)[C:9](=[O:37])[C:10]3[N:11]=[C:12]([CH2:22][NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[N:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:14]=3[N:15]=2)=[CH:5][CH:6]=1.[C:1]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:2]=[CH:3][C:4]([C:7]2[N:8]([C:38]3[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=3)[C:9](=[O:37])[C:10]3[N:11]=[C:12]([CH2:22][CH2:27][S:24]([NH2:23])(=[O:26])=[O:25])[N:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3[N:15]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 67282126HCID 67282126, compound

Product 2

HCID 57897836HCID 57897836, compoundHCID 86634698HCID 86634698, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-9-phenyl-6,9-dihydro-1H-purin-8-ylmethyl]-N-(4-methoxy-benzyl)-methanesulfonamide (18 mg, 0.026 mmol) in TFA (1 mL) was heated at 90° C. in a sealed tube for 12 h. The reaction mixture was concentrated in vacuo and the resulting crude oil was purified by flash chromatography (silica, 5% MeOH/CH2Cl2) to give the title compound Ar-[2-biphenyl-4-yl-1-(4-chloro-phenyl)-6-oxo-9-phenyl-6,9-dihydro-1H-purin-8-ylmethyl]-methanesulfonamide as a white solid. 1H NMR (CDCl3) δ (ppm) 7.64 7.54 (m, 3H), 7.51 7.45 (m, 4H), 7.44 7.38 (m, 4H), 7.37 7.30 (m, 4H), 7.28 (s, 1H), 7.13 (d, 2H), 5.92 (br s, 1H), 4.48 (s, 2H), 2.99 (s, 3H); HPLC-MS calculated for C31H24ClN5O3S (M+H+): 582.1. Found 582.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting crude oil was purified by flash chromatography (silica, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2a21d47aa49249a29d0d163407c44741
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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