Triethylamine → HCID 11538279, compound

HRID 2401550Notes

Reaction equation

HRID 2401550 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[N:14][C:15]=2Cl)[NH:10][C:9]1=[O:18])[C:2]1C=CC=CC=1.Cl.Cl.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([CH2:34][NH2:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.C(N(CC)CC)C>C(O)CCC>[NH3:8].[CH3:9][OH:18].[NH2:35][CH2:34][C:28]1([C:25]2[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=2)[CH2:33][CH2:32][N:31]([C:15]2[N:14]=[CH:13][N:12]=[C:11]3[C:16]=2[N:8]([CH2:1][CH3:2])[C:9](=[O:18])[NH:10]3)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24829100HCID 24829100, compoundHCID 86634683HCID 86634683, compound

Product 2

HCID 11538279HCID 11538279, compoundYield 109.3%HCID 21705897Ammonia methanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 7-benzyl-6-chloro-7,9-dihydropurin-8-one (0.015 g, 0.075 mmol), C-[4-(4-chlorophenyl)piperidin-4-yl]methylamine bis hydrochloride (0.025 g, 0.085 mmol) and triethylamine (0.11 mL, 0.85 mmol) in n-butanol (0.5 mL) was heated at 150° C. in a microwave reactor for 3 h. The cooled mixture was partitioned between ethyl acetate (30 mL) and water (5 mL) and the organic layer was dried, filtered and concentrated. Purification on SCX-II acid resin, eluting with methanol then 1M ammonia/methanol, gave 6-[4-aminomethyl-4-(4-chlorophenyl)piperidin-1-yl]-7-ethyl-7,9-dihydropurin-8-one as a cream solid (0.016 g, 0.041 mmol, 56%). LC-MS (LCT2) m/z 387 [M+H+], Rt 4.18 min.

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate (30 mL) and water (5 mL)
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on SCX-II acid resin
  6. washeluting with methanol

Sources & evidence

ORD record
ord-e196ab920fe24d1f9b8ad1e8caf6ccf3
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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