Piperidine → HCID 16065090, compound

HRID 1991138Notes

Reaction equation

HRID 1991138 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[N:15]=[C:16]([C:19]([OH:21])=O)[S:17][CH:18]=3)=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].C(N(CC)C(C)C)(C)C.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[N:15]=[C:16]([C:19]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:21])[S:17][CH:18]=3)=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 16065089HCID 16065089, compound

Product 1

HCID 16065090HCID 16065090, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 82 (60 mg, 0.20 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (50 mg, 0.39 mmol), piperidine (40 mg, 0.47 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP; 180 mg, 0.35 mmol). After stirring for 1 h, the reaction mixture was filtered and purified by preparative LCMS (column LUNA 10 g C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 83 as a white solid (42 mg, 0.11 mmol, 57%). 1H NMR (400 MHz, CDCl3) δ 0.89 (d, J=6.6 Hz, 2H), 1.63-1.76 (m, 6H), 1.86 (nonet, J=6.6 Hz, 1H), 2.56 (d, J=7.2 Hz, 2H), 3.69-3.75 (m, 2H), 4.32-4.39 (m, 2H), 7.45 (s, 1H), 7.70 (d, J=2.6 Hz, 1H), 8.11 (d, J=1.6 Hz, 1H), 8.13 (d, J=1.6 Hz, 1H), 9.26 (s, 1H). MS (CI) m/z 369 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified by preparative LCMS (column LUNA 10 g C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-2263c76e04c24eba9b86ea87c57cfef8
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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