Diisopropylethylamine → HCID 66673010, compound

HRID 423693Notes

Reaction equation

HRID 423693 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([O:10][C:11](Cl)=[O:12])[CH:2]=1.[CH3:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:26][N:25]=2)=[CH:20][CH:19]=1)(=[O:17])=[O:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[CH:26][C:27]([O:30][CH2:31][CH:32]3[CH2:37][CH2:36][N:35]([C:11]([O:10][C:3]4[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=4)=[O:12])[CH2:34][CH2:33]3)=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 597185862-[4-(Methylsulfonyl)phenyl]-5-(4-piperidinylmethoxy)pyridine

Product 1

HCID 66673010HCID 66673010, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloridocarbonate (268 mg, 1.33 mmol) was added to a mixture of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine (460 mg, 1.33 mmol), diisopropylethylamine (0.695 mL, 4 mmol) in CH2Cl2 (20 mL) at ambient temperature. The mixture was stirred at ambient temperature for 30 min, then concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 give 456 mg (67%) of 4-nitrophenyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.43 (d, 1H, J=2.7 Hz), 8.25 (d, 2H, J=9.2 Hz), 8.14 (d, 2H, J=8.5 Hz), 8.02 (d, 2H, J=8.5 Hz), 7.76 (d, 1H, J=8.7 Hz), 7.37-7.27 (m, 3H), 4.45-4.30 (m, 2H), 3.98 (d, 2H, J=5.1 Hz), 3.16-3.03 (m, 4H), 3.00-2.88 (m, 1H), 2.21-2.06 (m, 1H), 2.04-1.92 (m, 2H), 1.55-1.35 (m, 2H); LRMS (ESI), m/z 512 (M+H).

Workup

  1. concentrationconcentrated
  2. customthe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9d93cbef4110404e8fa3991bfaeb66d8
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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