Acetic Acid → 4-(8-((4-(2-methoxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholine

HRID 1945762Notes

Reaction equation

HRID 1945762 reaction equation
[CH3:1][O:2][C:3]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[N:14]([CH3:36])[C:15]3[C:20]([N:21]=2)=[C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:18]=[C:17]([NH:28][C:29]2[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:16]=3)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].[C:37](O)(=O)[CH3:38]>>[CH3:1][O:2][C:3]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[N:14]([CH3:36])[C:15]3[C:20]([N:21]=2)=[C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:18]=[C:17]([N:28]2[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[N:35]=[C:37]2[CH3:38])[N:16]=3)[CH2:8][CH2:7]1)([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 59605541N1-(8-((4-(2-methoxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-6-morpholino-9H-purin-2-yl)benzene-1,2-diamine

Product 1

HCID 596055814-(8-((4-(2-methoxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholineYield 21.1%

Procedure

A mixture of N1-(8-((4-(2-methoxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-6-morpholino-9H-purin-2-yl)benzene-1,2-diamine (177 mg, 0.368 mmol) in acetic acid (1.5 mL) was stirred at reflux for 5 hours. The reaction mixture was then concentrated and then purified first by flash chromatography (10% MeOH in DCM containing 1% 2 M ammonia in MeOH), followed by RP-HPLC to give 179 (0.0373 g, 21.1%). LCMS: M+H+=519.1.

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationThe reaction mixture was then concentrated
  3. custompurified first by flash chromatography (10% MeOH in DCM containing 1% 2 M ammonia in MeOH)

Sources & evidence

ORD record
ord-f459a238551747ab930171a06c2618f1
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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