Diisopropylethylamine → HCID 178474978, compound

HRID 1260706Notes

Reaction equation

HRID 1260706 reaction equation
Cl.[N:2]1([C:8]2[N:9]=[CH:10][CH:11]=[C:12]3[CH:16]=[CH:15][S:14][C:13]=23)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.O=[CH:27][CH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH:35][C:36](=[O:38])[CH3:37])[CH2:31][CH2:30]1>C1COCC1>[S:14]1[C:13]2=[C:8]([N:2]3[CH2:3][CH2:4][N:5]([CH2:27][CH2:28][C@H:29]4[CH2:34][CH2:33][C@H:32]([NH:35][C:36](=[O:38])[CH3:37])[CH2:31][CH2:30]4)[CH2:6][CH2:7]3)[N:9]=[CH:10][CH:11]=[C:12]2[CH:16]=[CH:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 426144467-(Piperazin-1-yl)thieno[2,3-c]pyridine hydrochlorideHCID 178474986HCID 178474986, compound

Product 1

HCID 178474978HCID 178474978, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution under Ar of commercially available 7-piperazine-1-yl-thieno[2,3-c]pyridine hydrochloride [CAS-No. 850734-85-9] (150 mg, 0.59 mmol) in THF (14 ml) were added subsequently iPr2NEt (0.1 ml, 0.59 mmol), trans-N-[4-(2-oxo-ethyl)-cyclohexyl]-acetamide [CAS-No. 946599-01-5, WO 2007/093540] (118 mg, 0.64 mmol) and Na(AcO)3BH (373 mg, 1.76 mmol). After stirring 18 h at room temperature the reaction mixture was partitioned between sat. aq. NaHCO3 sol. and EtOAc. The aqueous layer was extracted one more time with EtOAc. The combined organic layers were washed with H2O and brine and dried over MgSO4. After evaporation of the solvent, the crude product was purified by flash chromatography on silica gel (heptane to EtOAc) to yield the title compound as an off-white solid (82 mg, 36%), MS (ISP) m/z=387.2 [(M+H)+].

Workup

  1. customwas partitioned between sat. aq. NaHCO3 sol. and EtOAc
  2. extractionThe aqueous layer was extracted one more time with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvent
  6. customthe crude product was purified by flash chromatography on silica gel (heptane to EtOAc)

Sources & evidence

ORD record
ord-f6e6810f7b1c4f2a991dfe89ecc5e604
Source dataset
uspto-grants-2013_06
Patent number
US08470828B2

Reaction notes

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