Methylamine → (R)-3,N-Dimethyl-2-(5-nitro-1-oxo-1H-isoquinolin-2-yl)-butyramide

HRID 1161231Notes

Reaction equation

HRID 1161231 reaction equation
[CH3:1][CH:2]([CH3:21])[C@@H:3]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[N+:17]([O-:19])=[O:18])[C:8]1=[O:20])[C:4]([OH:6])=O.CN.O.O[N:26]1[C:30]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:21][CH:2]([CH3:1])[C@@H:3]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[N+:17]([O-:19])=[O:18])[C:8]1=[O:20])[C:4]([NH:26][CH3:30])=[O:6]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59515700(R)-3-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoic acid

Product 1

HCID 59515853(R)-3,N-Dimethyl-2-(5-nitro-1-oxo-1H-isoquinolin-2-yl)-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-3-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoic acid (2 g, 0.007 mol), methylamine (7 mL, 0.01 mol), 1-hydroxybenzotriazole hydrate (2 g, 0.01 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3 g, 0.01 mol), N,N-diisopropylethylamine (4 g, 0.03 mol) were stirred in methylene chloride (20 mL, 0.3 mol) at room temperature for 16 hours. The reaction mixture was diluted with CH2Cl2 (200 mL), washed with sat. NaHCO3, dried over MgSO4, filtered, purified via flash chromatoraphy (40 g of silica gel, 0-50% EtOAc/Hexane) to yield a yellow solid. m/z 304.2 (M+H)+.

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. custompurified via flash chromatoraphy (40 g of silica gel, 0-50% EtOAc/Hexane)
  5. customto yield a yellow solid

Sources & evidence

ORD record
ord-33f39442c4b941a6a25068412fdea871
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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