Hydrochloric Acid → HCID 23517375, compound

HRID 1836039Notes

Reaction equation

HRID 1836039 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1.Cl.[CH3:22][NH:23][O:24][CH3:25].CCN=C=NCCCN(C)C.Cl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:25][O:24][N:23]([CH3:22])[C:18]([C:4]1[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=[C:2]([OH:1])[CH:3]=1)=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22221627HCID 22221627, compound

Product 1

HCID 23517375HCID 23517375, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of acid 24 (0.35 g, 1.3 mmol), DMAP (0.5 g, 4.1 mmol), N,O Dimethylhydroxyl amine HCl (0.5 g, 5.1 mmol) in DMF (15 ml) was added EDCl (0.5 g, 2.6 mmol) and the reaction was stirred at rt for 1 hr. The reaction was then poured into 2N HCl and extracted with EtOAc, The EtOAc was dried, concentrated, and the resulting solid was triturated with CH2Cl2 and collected by filtration to give 119 as a white solid (0.22 g, 55%): Mp=125-127° C.; 1NMR (DMSO-d6) δ 9.88 (br s, 1 H), 9.44 (s, 1 H), 7.65(d, 2 H, 8.6 Hz), 7.08 (br s, 1 H), 6.97 (d, 1 H, J=2.3 Hz), 6.88 (d, 2 H, J=8.6 Hz), 6.71 (d, 1 H, J=2.6 Hz), 3.59 (s, 3 H), 3.30 (s, 3 H): MS 312 [M−H]−

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe EtOAc was dried
  3. concentrationconcentrated
  4. customthe resulting solid was triturated with CH2Cl2
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-91828341f6334bfc8b1f0ba4a9330107
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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