Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 23517383, compound

HRID 1794537Notes

Reaction equation

HRID 1794537 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20](O)=[O:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:27][O:26][N:25]([CH3:24])[C:20]([C:5]1[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[CH:8][C:7]=2[CH:19]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:21]

Participants

6

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10308394HCID 10308394, compound

Product 1

HCID 23517383HCID 23517383, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 23 (1.7 g, 5.7 mmol), N,O Dimethylhydroxyamine HCl (1.7 g, 17.1 mmol), DMAP (2.1 g, 17.1 mmol), and EDCl (1.9 g, 10 mmol) in DMF (30 ml) was stirred at rt for 1 hr. The reaction was then poured into 2 NHCl and extracted with EtOAc which was dried over MgSO4, concentrated, and the product was purified by column chromatography on silica gel (30% Et OAc/Hex) to give 121 as a solid (1.4 g, 74%); Mp=109–111° C.; 1H NMR (CDCl3) δ 7.77 (d, 2 H, J=8.7 Hz), 7.09 (d, 1 H, J=2.4 Hz), 6.99–6.95 (m, 3 H), 6.84 (s, 1 H), 3.86 (s, 6 H), 3.69 (s, 3 H), 3.40 (s, 3 H); MS 342 (M+H)+

Workup

  1. additionThe reaction was then poured into 2 NHCl
  2. extractionextracted with EtOAc which
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customthe product was purified by column chromatography on silica gel (30% Et OAc/Hex)

Sources & evidence

ORD record
ord-ba0045a69d6549afa5c94f293edce318
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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