(3-Nitro-pyridin-4-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine → N*4*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-3,4-diamine

HRID 273046Notes

Reaction equation

HRID 273046 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][C:12]1([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)([O-])=O>C(O)C.[Pd]>[N:28]1([CH2:27][CH2:26][CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([C:12]3([CH2:11][NH:10][C:9]4[CH:8]=[CH:7][N:6]=[CH:5][C:4]=4[NH2:1])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:19][CH:20]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 68578716(3-Nitro-pyridin-4-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine

Product 1

HCID 131727198N*4*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-3,4-diamineYield 36.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (3-Nitro-pyridin-4-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine (200 mg, 0.45 mmol) in ethanol (˜5 mL) was hydrogenated for 4 hours at room temperature at 40 psi in the presence of 10% Pd/C (20 mg, 10% w/w). The reaction mixture was filtered over Arbocel® and rinsed with ethanol. The filtrate was concentrated in vacuo to give a brown oily residue. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (94:6:0.6, by volume) to provide the title compound (68 mg, 36%). HRMS ESI+ m/z 411.2750 [MH]+.

Workup

  1. filtrationThe reaction mixture was filtered over Arbocel®
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a brown oily residue
  5. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (94:6:0.6, by volume)

Sources & evidence

ORD record
ord-e76b2d5f20964c7b80b279dd3303e198
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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