Methylamine → HCID 10236547, compound

HRID 896148Notes

Reaction equation

HRID 896148 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17]([NH2:19])=[O:18])[O:14][C:13]3=[O:20])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:21].[CH3:22]N>CO>[CH3:22][NH:19][C:17]([C@@H:15]1[O:14][C:13](=[O:20])[N:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:2]([CH3:1])[C:3](=[O:21])[CH2:4][O:5][C:6]=3[CH:11]=2)[CH2:16]1)=[O:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10149461HCID 10149461, compound

Product 1

HCID 10236547HCID 10236547, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of (5R)-3-(3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazin-7-yl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester (EXAMPLE 59, Step 3, 200 mg, 0.65 mmol) in MeOH (5 mL) is added MeNH2 (5 mL, 10 mmol, 2 M solution in MeOH). The resulting solution is stirred for 3 h at room temperature at which time the resulting white precipitate is filtered, washed with additional MeOH (5 mL), and dried under high vacuum to give the title compound (153 mg, 77%); 1H NMR (300 MHz, DMSO) δ 8.56 (br t, 1H), 7.50 (d, 1H), 7.41-7.33 (m, 2H), 5.23 (dd, 1H), 4.85 (s, 2H), 4.45 (dd, 1H), 4.15 (dd, 1H), 3.45 (s, 3H), 2.84 (d, 2H); MS for C14H15N3O5 m/z 306.5 (M+H)+.

Workup

  1. filtrationis filtered
  2. washwashed with additional MeOH (5 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-0e7ad546a81d475598f161e991cda42f
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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