Hydrochloric Acid → HCID 178502660, compound

HRID 1094633Notes

Reaction equation

HRID 1094633 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.CN([C:17]([O:21][N:22]1N=NC2C=CC=C[C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C>>[CH3:17][O:21][N:22]([CH3:23])[C:10]([C:7]1[CH:8]=[CH:9][C:4]2[N:3]=[N:2][NH:1][C:5]=2[CH:6]=1)=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1146TrimethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524186HCID 178524186, compound

Product 1

HCID 178502660HCID 178502660, compound

Procedure

A mixture of 1H-1,2,3-benzotriazole-6-carboxylic acid (Aldrich, 500 mg, 3.1 mmol), N,O-dimethylhydroroxylamine hydrochloride (Aldrich, 299 mg, 3.1 mmol), HBTU (1.5 g, 4.0 mmol) and trimethylamine (1.28 ml, 9.2 mmol) were added and the mixture was stirred for 18 hours at room temperature. Then, evaporation, purification through silica gel column chromatography eluting with DCM/MeOH (10:1) to give N-methoxy-N-methyl-1H-1,2,3-benzotriazole-6-carboxamide (LC-MS (MS (ESI) m/z 205 (M−H)−, 207 (M+H)+). To a THF (50 ml) solution of the product was added 0.96 M hexane solution of ethylmagnesium bromide (15 ml, 14.4 mmol) at 0° C., and the mixture was stirred for 16 hours at room temperature. Then the reaction was quenched with aqueous solution of ammonium chloride and the product was extracted with AcOEt, washed with brine, dried over magnesium sulfate. Then, evaporation in vacuo gave 1-(1H-1,2,3-benzotriazol-6-yl)propan-1-one (LC-MS (MS (ESI) m/z 174 (M−Hy, 176 (M+H)+).

Workup

  1. additionwere added
  2. customThen, evaporation, purification through silica gel column chromatography
  3. washeluting with DCM/MeOH (10:1)

Sources & evidence

ORD record
ord-e8f60571dc25467f88d74d92c6afbe0c
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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