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

HRID 1923318Notes

Reaction equation

HRID 1923318 reaction equation
[CH:1]([C:4]1[N:8]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([C:19]4([O:25][CH3:26])[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)[N:15]3[CH3:18])=[C:11]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:10]=2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]=2[N:5]=1)([CH3:3])[CH3:2].[CH3:37][S:38]([CH:41]=[CH2:42])(=[O:40])=[O:39]>O>[CH:1]([C:4]1[N:8]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([C:19]4([O:25][CH3:26])[CH2:24][CH2:23][CH2:22][N:21]([CH2:42][CH2:41][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:20]4)[N:15]3[CH3:18])=[C:11]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[N:10]=2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 596052822-(2-Isopropylbenzoimidazol-1-yl)-8-(3-methoxypiperidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine

Product 1

HCID 596054514-(2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-8-(3-methoxy-1-(2-(methylsulfonyl)ethyl)piperidin-3-yl)-9-methyl-9H-purin-6-yl)morpholineYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-isopropylbenzoimidazol-1-yl)-8-(3-methoxypiperidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine (150 mg, 0.31 mmol) and methanesulfonylethene (32 μL, 0.37 mmol) in IMS (5 mL) was allowed to stir for 4 h at room temp. before pouring the reaction mixture into H2O. The resulting precipitate was collected by filtration and dried under vacuum affording 713 (141 mg, 77%). LCMS (method I): RT 2.82 min, [M+H]+ 597.2. 1H NMR (DMSO, 400 MHz): δ 7.92-7.91 (1 H, m), 7.65-7.64 (1 H, m), 7.24-7.23 (2 H, m), 4.25 (4 H, brd s), 4.00-3.85 (4 H, m), 3.8-3.75 (4 H, m), 3.40-3.20 (2 H, m), 3.15-3.00 (4 H, m), 2.95 (3 H, s), 2.81-2.76 (4 H, m), 2.30-2.20 (1 H, m), 2.10-2.95 (2 H, m), 1.84-1.74 (2 H, m), 1.36 (6 H, dd, J=6.77, 2.96 Hz)

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a3e4671d692e405095c68eb7b2d5b9e5
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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