Diisopropylethylamine → 5-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-benzoylpiperidine-1-yl)-thiazolo[5,4-d]pyrimidine

HRID 1396729Notes

Reaction equation

HRID 1396729 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.Cl.[C:34]([CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([N:45]2[CH2:46][CH2:47][CH:42]([C:34](=[O:41])[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:43][CH2:44]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27244374-Benzoylpiperidine hydrochlorideHCID 509418672-(4-Fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine

Product 1

HCID 469168505-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-benzoylpiperidine-1-yl)-thiazolo[5,4-d]pyrimidineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-methanesulfonyl-thiazolo[5,4-d]pyrimidine (50 mg, 0.14 mmol) in acetonitrile (5 ml) was added diisopropylethylamine (0.45 mmol, 74 μL) and 4-benzoylpiperidine hydrogen chloride (0.15 mmol). The reaction mixture was stirred at room temperature for 16 hours whereupon the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 1% CH3OH in CH2Cl2), yielding the pure title compound (59 mg) which was characterized by its mass spectrum: MS m/z (%): 462 ([M+H]+, 100).

Workup

  1. customwas removed in vacuo
  2. customThe resulting residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-63e976ed24c6497bb1580cd398a28e5f
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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