Cyclohexanecarboxaldehyde → N-{(1S,2R,3S,4R)-4-[2-{N'-[1-Cyclohexyl-methylidene]-hydrazino}-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 2382425Notes

Reaction equation

HRID 2382425 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([NH:19][NH2:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:21]2[CH2:25][C@H:24]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[C@@H:23]([OH:31])[C@H:22]2[OH:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:39]1([CH:45]=O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CO>[CH:39]1([CH:45]=[N:20][NH:19][C:17]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[C@@H:21]3[CH2:25][C@H:24]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[C@@H:23]([OH:31])[C@H:22]3[OH:32])=[C:10]([NH:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:18]=2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 66630796N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Product 1

HCID 66630748N-{(1S,2R,3S,4R)-4-[2-{N'-[1-Cyclohexyl-methylidene]-hydrazino}-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-{4-[6-(2,2-diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (step 1) (0.1 g, 0.19 mmol) in dry methanol (5 ml) is added cyclohexane carboxaldehyde (0.026 g, 0.23 mmol). The reaction mixture is heated at reflux for 12 h. The reaction mixture is concentrated in vacuo purification by preparative TLC affords the title compound. LC-MS (0.1% formic acid, acetonitrile): (MH+ 611.45)

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction mixture is concentrated in vacuo purification by preparative TLC

Sources & evidence

ORD record
ord-aee8cefe385c493aa733fc70c0c8756c
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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