Triethylamine → 3,5-Diamino-6-chloropyrazine-2-carboxylic-acid(1-aza-bicyclo[2.2.2]oct-3-yl)-amide

HRID 509912Notes

Reaction equation

HRID 509912 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.Cl.Cl.[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH:17]([NH2:23])[CH2:16]2.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH:17]([NH:23][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:12])[CH2:16]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 64521193,5-Diamino-6-chloro-pyrazine acid2×

Product 1

HCID 1178563693,5-Diamino-6-chloropyrazine-2-carboxylic-acid(1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-diamino-6-chloropyrazine-2-carboxylic acid (Intermediate 1.1.1, 2.50 g, 13.1 mmol), 1-aza-bicyclo[2.2.2]oct-3-ylamine dihydrochloride (2.87 g, 14.4 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (4.62 g, 14.4 mmol) and triethylamine (6.72 mL, 39.3 mmol) in dry N,N-dimethylformamide (25 mL) is stirred overnight at room temperature under nitrogen atmosphere. The resulting solid is collected by filtration, washed with diethyl ether and dried at 50° C. under vacuum.

Workup

  1. filtrationThe resulting solid is collected by filtration
  2. washwashed with diethyl ether
  3. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-9780cb66fb244caf853b5f8d4dd5ddd1
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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