Diisopropylamine → HCID 69006576, compound

HRID 1963726Notes

Reaction equation

HRID 1963726 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([NH:19][CH3:20])[C:16]([N+:21]([O-:23])=[O:22])=[CH:15][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12](O)=[O:13])[CH:7]=1.C[N:25](C)CCCN=C=NCC.N1C2C(=NC=CC=2)N(O)N=1.C(NC(C)C)(C)C.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([NH:19][CH3:20])[C:16]([N+:21]([O-:23])=[O:22])=[CH:15][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([NH2:25])=[O:13])[CH:7]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 181649HOAtHCID 690019044-(2-Methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylic acid

Product 1

HCID 69006576HCID 69006576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture containing 4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylic acid (1 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (2 eq), 3H-1,2,3-triazolo[4,5-b]pyridine-3-ol (1.5 eq), and diisopropylamine (5 eq) in tetrahydrofuran was stirred at room temperature for 1 hour. To this was then added ammonium chloride (2 eq) and the resulting mixture was stirred together for 48 hours. Reaction concentrated. Purification on silica gel, 50% acetone in hexanes to yield 4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxamide as a bright yellow solid. HPLC=3.70 min; MS: MH+=319.

Workup

  1. customReaction
  2. concentrationconcentrated
  3. customPurification on silica gel, 50% acetone in hexanes

Sources & evidence

ORD record
ord-2cce82f46750474383c32dda6adeb756
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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