Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 76171765, compound

HRID 1244126Notes

Reaction equation

HRID 1244126 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:22]3[CH:17]([NH:18][C:19](=[O:26])[C:20]([C:24]#[N:25])=[C:21]3[OH:23])[S:16][CH:15]=2)=[CH:10][CH:9]=1)=O.[C:27]([O-:30])(=[O:29])C.[Na+]>O>[C:24]([C:20]1[C:19](=[O:26])[NH:18][CH:17]2[S:16][CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH:2]=[N:3][O:4][CH2:5][C:27]([OH:30])=[O:29])=[CH:13][CH:12]=3)[CH:22]2[C:21]=1[OH:23])#[N:25]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 54689900HCID 54689900, compound

Product 1

HCID 76171765HCID 76171765, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,O-Dimethylhydroxylamine hydrochloride (0.067 g, 0.3 mmol) was added to a room temperature solution of 3-(4-Formyl-phenyl)-4-hydroxy-6-oxo-3a,6,7,7a-tetrahydro-thieno[2,3-b]pyridine-5-carbonitrile (0.1 g, 0.29 mmol) and sodium acetate (0.025 g, 0.3 mmol) in 1:1:1 mixture of methanoldioxane/water (6 mL). The reaction mixture was quenched with 3N HCl after complete reaction, extracted with ethyl acetate (3×20 mL), organic extracts washed with brine, dried (MgSO4) and concentrated to a brown solid. MS (ESI) m/e 369.5 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.30 (br s, 1H), 8.36 (s, 1H), 7.59 (d, J=9, 2H), 7.47 (d, J=9, 2H), 7.03 (s, 1H), 4.66 (s, 2H).

Workup

  1. customThe reaction mixture was quenched with 3N HCl
  2. customafter complete reaction
  3. extractionextracted with ethyl acetate (3×20 mL), organic extracts
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a brown solid

Sources & evidence

ORD record
ord-bb057e3823eb4e88ba562098c9ada0af
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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