2-(Oxan-4-yl)ethan-1-amine → HCID 69216609, compound

HRID 272721Notes

Reaction equation

HRID 272721 reaction equation
Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[NH:7][C:8](=[O:17])[C:9]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]=3[NH:11][C:5]=2[CH:4]=1.[O:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][NH2:28])[CH2:22][CH2:21]1>O1CCOCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:9]2[C:8](=[O:17])[NH:7][C:6]3[CH:18]=[CH:19][C:3]([CH2:2][NH:28][CH2:27][CH2:26][CH:23]4[CH2:24][CH2:25][O:20][CH2:21][CH2:22]4)=[CH:4][C:5]=3[NH:11][C:10]=2[CH:12]=1

Participants

4

Reactant 2

HCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 69219731HCID 69219731, compound

Product 1

HCID 69216609HCID 69216609, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 512A (50 mg, 0.15 mmol) and 2-(tetrahydro-pyran-4-yl)-ethylamine (38.3 mg, 0.30 mmol) in dioxane (2.0 mL) was heated 11 hours at 50° C., cooled to room temperature, and concentrated under vacuum. The residue was purified by preparative HPLC to give 30.3 mg (53%) of the desired product. 1H NMR (300 MHz, DMSO-d6) □ 10.05 (s, 1H), 8.56 (br s, 1H), 8.16 (s, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.11 (d, J=2.0 Hz, 1H), 7.00-7.08 (m, 3H), 6.97 (dd, J=2.0, 8.5 Hz, 1H), 4.00-4.04 (m, 2H), 3.78-3.86 (m, 2H), 3.20-3.30 (m, 3H), 2.88-3.00 (m, 2H), 1.49-1.58 (m, 4H), 1.11-1.19 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3afbb23af438415fadd1cff5766dce7e
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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