Dichloromethane → Methyl 2-(4-(2-(2-ethyl-1h-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9h-purine-8-carbonyl)piperidin-1-yl)-2-methylpropanoate

HRID 1923224Notes

Reaction equation

HRID 1923224 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]([OH:32])[CH:19]4[CH2:24][CH2:23][N:22]([C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]4)[N:14]3[CH3:17])=[C:10]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:9]=2)[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]=2[N:4]=1)[CH3:2].C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:24]4)=[O:32])[N:14]3[CH3:17])=[C:10]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:9]=2)[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]=2[N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 59606022racemic methyl 2-(4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidin-1-yl)-2-methylpropanoate

Product 1

HCID 59605225Methyl 2-(4-(2-(2-ethyl-1h-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9h-purine-8-carbonyl)piperidin-1-yl)-2-methylpropanoateYield 64%

Procedure

To a solution of racemic methyl 2-(4-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)(hydroxy)methyl)piperidin-1-yl)-2-methylpropanoate, from the procedures for 526 and 527, (0.115 g, 0.199 mmol) in methylene chloride (5.0 mL, 78 mmol) was added Dess-Martin periodinane (0.0930 g, 0.219 mmol). The resulting mixture was then stirred at room temp. for 1 hour. The reaction mixture was filtered though paper to remove all solid precipitates and then concentrated. The residue was then purified by RP-HPLC to give 528 (52 mg, 64%). LCMS m/z: 288.3 (2M+H+)

Workup

  1. filtrationThe reaction mixture was filtered though paper
  2. customto remove all solid
  3. customprecipitates
  4. concentrationconcentrated
  5. customThe residue was then purified by RP-HPLC

Sources & evidence

ORD record
ord-3c50d7d1dc464ec79ab85b18594bdfbc
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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