Hydrochloric Acid → HCID 23517375, compound

HRID 1794535Notes

Reaction equation

HRID 1794535 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>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 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 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 EDCI (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), 688 (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-522e0872977c4b1eb01089deb906f3ec
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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