Diisopropylethylamine → HCID 58515996, compound

HRID 717862Notes

Reaction equation

HRID 717862 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[N:29]3[CH:30]=[N:31][CH:32]=[C:28]3[C:27]([Br:33])=[CH:26][C:25]=2[CH:34]([NH2:36])[CH3:35])[CH2:20][CH2:19]1)(=[O:17])[CH3:16].Br[C:38]1[N:46]=[CH:45][N:44]=[C:43]2[C:39]=1[N:40]=[CH:41][N:42]2[CH:47]1[CH2:52][CH2:51][CH2:50][CH2:49][O:48]1.C(N(CC)C(C)C)(C)C>C(O)C>[C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[N:29]3[CH:30]=[N:31][CH:32]=[C:28]3[C:27]([Br:33])=[CH:26][C:25]=2[CH:34]([NH:36][C:38]2[N:46]=[CH:45][N:44]=[C:43]3[C:39]=2[N:40]=[CH:41][N:42]3[CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[CH3:35])[CH2:20][CH2:19]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purineHCID 86659300HCID 86659300, compound

Product 1

HCID 58515996HCID 58515996, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[5-(4-acetylpiperazin-1-yl)-8-bromoimidazo[1,5-a]pyridin-6-yl]ethanamine bis(trifluoroacetate) (67 mg, 0.11 mmol), 6-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (48 mg, 0.17 mmol), and N,N-diisopropylethylamine (98 mL, 0.56 mmol) in ethanol (0.87 mL) was heated at 95° C. overnight. Purification via preparative HPLC on a C-18 column eluting acetonitrile: water gradient buffered with ammonia to pH 10 gave the desired product (36 mg, 56%). LCMS for C25H31BrN9O2 (M+H)+: m/z=568.2, 570.2. Found: 568.0, 570.0.

Workup

  1. customPurification via preparative HPLC on a C-18 column
  2. washeluting acetonitrile

Sources & evidence

ORD record
ord-86f7bde102424067bbeaeffc54cf7a51
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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