Methyl vinyl sulfone → 4-(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-8-(3-methoxy-1-(2-(methylsulfonyl)ethyl)azetidin-3-yl)-9-methyl-9H-purin-6-yl)morpholine

HRID 1946181Notes

Reaction equation

HRID 1946181 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]4([O:22][CH3:23])[CH2:21][NH:20][CH2:19]4)[N:14]3[CH3:17])=[C:10]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:9]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1)[CH3:2].[CH3:34][S:35]([CH:38]=[CH2:39])(=[O:37])=[O:36]>>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]4([O:22][CH3:23])[CH2:21][N:20]([CH2:39][CH2:38][S:35]([CH3:34])(=[O:37])=[O:36])[CH2:19]4)[N:14]3[CH3:17])=[C:10]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:9]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 596058342-(2-Ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine

Product 1

HCID 596057024-(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-8-(3-methoxy-1-(2-(methylsulfonyl)ethyl)azetidin-3-yl)-9-methyl-9H-purin-6-yl)morpholineYield 68%

Procedure

To a solution of 2-(2-ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine (100 mg, 0.22 mmol) in IMS (2 mL) was added methanesulfonylethene (21 μL, 0.25 mmol) and the resulting mixture allowed to stir at r.t. for 18 h. The reaction mixture was concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%). The resulting residue was triturated with EtOAc and cyclohexane and the resulting solid dried in vacuo affording 826 (83 mg, 67%). LCMS (method I): RT 2.65 min, [M+H]+ 555.3. 1H NMR (DMSO, 400 MHz): δ 8.05-8.05 (1 H, m), 7.64-7.63 (1 H, m), 7.26-7.25 (2 H, m), 4.27 (4 H, brd s), 4.02 (2 H, d, J=7.94 Hz), 3.79 (4 H, t, J=4.57 Hz), 3.72 (3 H, s), 3.42 (2 H, d, J=7.99 Hz), 3.28-3.25 (2 H, m), 3.17 (2 H, t, J=6.52 Hz), 3.05 (3 H, s), 2.89 (2 H, t, J=6.53 Hz), 1.40 (3 H, s), 1.35 (3 H, t, J=7.43 Hz)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)
  3. customThe resulting residue was triturated with EtOAc and cyclohexane
  4. customthe resulting solid dried in vacuo

Sources & evidence

ORD record
ord-91c039d68298442db4c1ded4e27a6117
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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