2-Amino-6-Chloropyrazine → 6-chloro-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyrazin-2-amine

HRID 254752Notes

Reaction equation

HRID 254752 reaction equation
O([BH-](OC(C)=O)OC(C)=O)C(C)=O.[Na+].[Cl:15][C:16]1[N:21]=[C:20]([NH2:22])[CH:19]=[N:18][CH:17]=1.[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:32]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1>ClCCCl.CC(O)=O>[Cl:15][C:16]1[N:21]=[C:20]([NH:22][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:29]([O:28][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:30]=2)[CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 3

HCID 1184582-Amino-6-ChloropyrazineHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866142996-chloro-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyrazin-2-amineYield 10%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Sodium triacetoxyl-borohydride (1315 mg, 6.2 mmol) was added to a solution of 6-chloro-pyrazin-2-yl-amine (400 mg, 3.10 mmol) and 3-cyclopentyloxy-4-methoxybenzaldehyde (818 mg, 3.7 mmol) in 50 ml of DCE, 1 ml of HOAc was added and the mixture was stirred overnight at 50° C., followed by addition of another 50 ml of DCE. The organic phase was washed with water, and the product was purified with column (silica gel, hexane:EtOAc 6:1) to give 50 mg of (6-chloro-pyrazin-2-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine, yield 10%.

Workup

  1. additionwas added
  2. washThe organic phase was washed with water
  3. customthe product was purified with column (silica gel, hexane:EtOAc 6:1)

Sources & evidence

ORD record
ord-6724f67941c6401a838464c37a55200a
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

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