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 1882577Notes

Reaction equation

HRID 1882577 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-71da32e351004d3eae8c1cea3269356d
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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