Trifluoroacetic acid → N-(1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethyl)-9H-purine-6-amine

HRID 1192506Notes

Reaction equation

HRID 1192506 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH2:24])[CH3:23])[C:19]([N:25]2[CH2:29][CH2:28][CH2:27][C@@H:26]2[CH2:30][O:31][CH3:32])=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2.C(N(CC)C(C)C)(C)C.C(O)(C(F)(F)F)=O>C(O)C>[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH:24][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:23])[C:19]([N:25]2[CH2:29][CH2:28][CH2:27][C@@H:26]2[CH2:30][O:31][CH3:32])=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 673009761-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamineHCID 178419477HCID 178419477, compound

Product 1

HCID 178495643N-(1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethyl)-9H-purine-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.0174 g, 0.0876 mmol), 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine (0.014 g, 0.044 mmol), and N,N-diisopropylethylamine (0.01525 mL, 0.0876 mmol) in ethanol (0.1 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/minute) to give the product as a mixture of diastereoisomers (bis-TFA salts). LCMS calculated for C22H25ClN7O(M+H)+: m/z=438.2; found: 438.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resultant residue was purified on RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/minute)
  6. customto give the product

Sources & evidence

ORD record
ord-542139dd44bb4746bd9193dc18bed8be
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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