(3-Nitro-pyridin-2-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine → N*2*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-2,3-diamine

HRID 273048Notes

Reaction equation

HRID 273048 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][C:12]2([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:20][CH:19]=3)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:6][CH:7]=[CH:8][CH:9]=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:5]4[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=4)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[CH:19][CH:20]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 68578573(3-Nitro-pyridin-2-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine

Product 1

HCID 131727199N*2*-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-pyridine-2,3-diamineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (3-Nitro-pyridin-2-yl)-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine (465 mg, 1.06 mmol) in ethanol (˜10 mL) was hydrogenated for 4 hours at room temperature at 40 psi in the presence of 10% Pd/C (45 mg, 10% w/w). The reaction mixture was filtered over Arbocel® and rinsed with ethanol (30 mL), 2M HCl (20 mL) and EtOH (30 mL). The filtrate was concentrated in vacuo to give the title compound (365 mg, 84%). HRMS ESI+ m/z 411.2750 [MH]+.

Workup

  1. filtrationThe reaction mixture was filtered over Arbocel®
  2. washrinsed with ethanol (30 mL), 2M HCl (20 mL) and EtOH (30 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9339f7fb1c6c4d2e89c04b47674c0190
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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