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

HRID 1836041Notes

Reaction equation

HRID 1836041 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% EtOAc/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% EtOAc/Hex)

Sources & evidence

ORD record
ord-b4c7b2edd1a241ccbee987f9278c642d
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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