Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58918011, compound

HRID 1896543Notes

Reaction equation

HRID 1896543 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[C:8]([C:10](O)=[O:11])[S:9][C:5]=2[CH:4]=1.CN([C:20]([O:24][N:25]1N=NC2C=CC=N[C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:20][O:24][N:25]([CH3:26])[C:10]([C:8]1[S:9][C:5]2[CH:4]=[C:3]([C:2]([F:16])([F:15])[F:1])[CH:14]=[CH:13][C:6]=2[CH:7]=1)=[O:11]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 179795236-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 58918011HCID 58918011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid dissolved in DMF (0.5 M) was added HATU (1.2 equiv) at 0° C. and the reaction was stirred for 2 min followed by addition of N,O-dimethylhydroxylamine hydrochloride (1.5 equiv). The reaction was stirred for 2 min prior to the addition of iPr2NEt (5 equiv). The reaction was stirred for an additional 20 min at 0° C. The reaction was quenched with equivalent amounts of half-saturated aqueous NaHCO3 and H2O. The title compound was obtained as a solid and filtered on a Büchner funnel before being and air-dried.

Workup

  1. stirringThe reaction was stirred for 2 min
  2. stirringThe reaction was stirred for an additional 20 min at 0° C
  3. customThe reaction was quenched with equivalent amounts of half-saturated aqueous NaHCO3 and H2O

Sources & evidence

ORD record
ord-d0b46c944c424939ab006e0ec4e3f957
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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