Triethylamine → HCID 44476316, compound

HRID 2192515Notes

Reaction equation

HRID 2192515 reaction equation
[OH:1][NH:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[NH:4].[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH:26]([CH3:28])[CH3:27])[C:19](Cl)=O.C(N(CC)CC)C>CN(C)C=O>[Cl:15][C:16]1[CH:17]=[C:18]([C:19]2[O:1][N:2]=[C:3]([C:5]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:6]=3[CH:7]=[CH:8][N:9]=[CH:10]4)[N:4]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH:26]([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21710470HCID 21710470, compoundHCID 178513273HCID 178513273, compound

Product 1

HCID 44476316HCID 44476316, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-hydroxy-5-isoquinolinecarboximidamide (D1; 1.18 g, 6.30 mmol) was added to a solution of 3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (D4; 1.54 g, 6.62 mmol), triethylamine (0.966 ml, 6.93 mmol) and N,N-dimethylformamide (DMF) (10 ml) at 0° C. under a blanket of nitrogen. The mixture was allowed to warm to room temperature over 1 h and then heated at 120° C. under nitrogen overnight. The mixture was allowed to cool and then filtered. An off-white solid was collected and washed with acetonitrile to give the title compound (2.01 g).

Workup

  1. temperatureheated at 120° C. under nitrogen overnight
  2. temperatureto cool
  3. filtrationfiltered
  4. customAn off-white solid was collected
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-6c09aeb9f1e84821b0484e50c19e5d9a
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…