Trifluoroacetic acid → HCID 178463606, compound

HRID 1192471Notes

Reaction equation

HRID 1192471 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Br)[N:3]=1.[F:12][C:13]1[CH:14]=[C:15]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[CH:29]([NH2:31])[CH3:30])[CH:16]=[N:17][CH:18]=1.C(N(CC)C(C)C)(C)C.C(O)(C(F)(F)F)=O>C(O)C>[F:12][C:13]1[CH:14]=[C:15]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[CH:29]([NH:31][C:4]2[N:3]=[C:2]([NH2:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][NH:8]3)[CH3:30])[CH:16]=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 61011392-Amino-6-bromopurineHCID 67248618HCID 67248618, compound

Product 1

HCID 178463606HCID 178463606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-6-bromopurine (0.030 g, 0.14 mmol), 1-[1-(5-fluoropyridin-3-yl)-2-naphthyl]ethanamine (0.019 g, 0.07 mmol), and N,N-diisopropylethylamine (0.01465 mL, 0.084 mmol) in ethanol (0.2 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 rotomers (bis-TFA salt). LCMS calculated for C22H19FN7(M+H)+: m/z=400.2; found: 400.0.

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-632ca04f1d264813ac6a21b18be6fbf6
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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