1,2-Diaminocyclohexane, trans- → HCID 71295561, compound

HRID 1776880Notes

Reaction equation

HRID 1776880 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7](=[NH:10])OC.[C@@H:14]1(N)[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[NH2:20]>CCO>[Br:1][C:2]1[CH:11]=[C:6]([C:7]2[NH:20][C@@H:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]3[N:10]=2)[C:5]([O:12][CH3:13])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 438061,2-Diaminocyclohexane, trans-HCID 86728275HCID 86728275, compound

Product 1

HCID 71295561HCID 71295561, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 5-bromo-2-methoxynicotinimidate (6.1 g, 18.5 mmol) in EtOH (100 mL) was added trans-Cyclohexane-1,2-diamine (2.1 g, 18.5 mmol) at room temperature, the mixture was stirred at 80° C. for 12 hours. The solvent was removed and the resulting residue was washed with dichloromethane (50 mL*2), then dry to provide trans-2-(5-bromo-2-methoxypyridin-3-yl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazole (4 g, yield 70.2%). 1HNMR (400 MHz, CDCl3) δ 8.56 (d, J=2.4 Hz, 1H), 8.43 (s, J=2.4 Hz, 1H), 4.14 (s, 3H), 3.51˜3.53 (m, 2H), 2.45˜2.49 (m, 2H), 1.91˜1.93 (m, 2H), 1.61˜1.63 (m, 2H), 1.36˜1.41 (m, 2H), 1.25 (s, 1H). MS (M+H)+: 310/312.

Workup

  1. customThe solvent was removed
  2. washthe resulting residue was washed with dichloromethane (50 mL*2)
  3. customdry

Sources & evidence

ORD record
ord-735de0ba8ca24e09b83e3268cd2cf283
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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