Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86658353, compound

HRID 340150Notes

Reaction equation

HRID 340150 reaction equation
CCN(C(C)C)C(C)C.CN([C:13]([O:17][N:18]1N=NC2C=CC=C[C:19]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:34][C:35]1[CH:46]=[CH:45][C:38]2[C:39]([C:42](O)=[O:43])=[N:40][S:41][C:37]=2[CH:36]=1.Cl.CNOC>CN(C=O)C>[Br:34][C:35]1[CH:46]=[CH:45][C:38]2[C:39]([C:42]([N:18]([O:17][CH3:13])[CH3:19])=[O:43])=[N:40][S:41][C:37]=2[CH:36]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534011926-Bromobenzo(d)isothiazole-3-carboxylic acid

Product 1

HCID 86658353HCID 86658353, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (11.7 mL, 67.4 mmol) and HBTU (7.03 g, 18.5 mmol) were added to a solution of 6-bromobenzo[d]isothiazole-3-carboxylic acid (4.35 g, 16.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.14 g, 21.9 mmol) in DMF (100 mL). The reaction was stirred at room temperature for 2 hours. The mixture was partitioned between water and EtOAc. The organic layer was washed with aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (hexane:EtOAc, 3:1) to give 6-bromo-N-methoxy-N-methylbenzo[d]isothiazole-3-carboxamide (4.60 g, 91%) as a solid. 1H NMR (CDCl3, 400 MHz) δ □8.12 (m, 2H), 8.59 (d, J=8.8 Hz, 1H), 3.83 (s, 3H), 3.49 (s, 3H).

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with aqueous NaHCO3 solution and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane:EtOAc, 3:1)

Sources & evidence

ORD record
ord-b5fa795e169f4a188336763b544bc8a6
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

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