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

HRID 521391Notes

Reaction equation

HRID 521391 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-931871004cf14616bdea1587be4a4d23
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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