Isopropylamine → HCID 67281915, compound

HRID 1616148Notes

Reaction equation

HRID 1616148 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)=[O:4].[CH:17]([N:20](CC)C(C)C)([CH3:19])[CH3:18].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CC(N)C>ClCCl>[CH:17]([NH:20][C:9]([C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15])=[O:11])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219064744-(Methoxycarbonyl)-2-nitrobenzoic acid

Product 1

HCID 67281915HCID 67281915, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(methoxycarbonyl)-2-nitrobenzoic acid (0.50 g, 2.22 mmol) in dichloromethane (20 mL) was added N,N-diisopropylethylamine (1.16 mL, 6.66 mmol) and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.89 g, 2.33 mmol). The reaction mixture was stirred for 15 min. Propan-2-amine (0.20 mL, 2.33 mmol) was added and the reaction mixture was stirred at rt overnight. The reaction mixture was then concentrated and the crude residue was purified by flash silica gel chromatography (30% to 60% EtOAc/hexanes) to afford methyl 4-[(isopropylamino)carbonyl]-3-nitrobenzoate (0.48 g, 80%). LC-MS: (FA) ES+ 268.

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. concentrationThe reaction mixture was then concentrated
  3. customthe crude residue was purified by flash silica gel chromatography (30% to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8e2fa94a20f042c49418370dffc7a9bc
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

Loading…