HCID 86694688, compound → HCID 86694736, compound

HRID 475238Notes

Reaction equation

HRID 475238 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](=[N:19]O)[CH2:17][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1>C1COCC1.[Ni]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]([NH2:19])[CH2:17][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1

Participants

4

Reactant 1

HCID 86694688HCID 86694688, compound

Product 1

HCID 86694736HCID 86694736, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 172 (30 mg, 0.11 mmol) in THF (3 mL) was added Raney-Ni (50 mg) and the mixture was stirred at RT overnight, filtered and concentrated in vacuo. Purification by HPLC afforded 10 mg (35%) of 1-(1-tetrahydropyran-2-ylbenzimidazol-5-yl)propan-1-amine (174) as a colourless oil: 1H NMR (400 MHz, CDCl3): δ 7.98 (m, 1H), 7.64 (m, 1H), 7.40 (m, 1H), 7.14-7.36 (m, 1H), 5.40-5.45 (m, 1H), 4.06 (m, 1H), 3.85 (m, 1H), 3.70 (m, 1H), 2.02-2.10 (m, 3H), 1.62-1.72 (m, 8H), 0.77-0.84 (m, 3H); MS (ESI+) m/z=260 [M+1]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-3ff151c8214e486cbac60c009cfcd65f
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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