2,2-dimethyl-N-prop-2-ynyl-propionamide → HCID 86622782, compound

HRID 1965978Notes

Reaction equation

HRID 1965978 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[CH3:27][C:28]([CH3:36])([CH3:35])[C:29]([NH:31][CH2:32][C:33]#[CH:34])=[O:30]>CN(C=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:34]#[C:33][CH2:32][NH:31][C:29](=[O:30])[C:28]([CH3:36])([CH3:35])[CH3:27]

Participants

4

Reactant 2

HCID 110517292,2-dimethyl-N-prop-2-ynyl-propionamideHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86622782HCID 86622782, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

Use a method similar to the General Procedure 3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (212 mg, 0.5 mmol) and 2,2-dimethyl-N-prop-2-ynyl-propionamide (139 mg, 1 mmol) (prepared by following the procedure described in Org. Lett. 2004, 6, 3593) in DMF/triethylamine (5:1, 6 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1 to 7:3 gradient) to obtain 7-chloro-6-[3-(2,2-dimethyl-propionylamino)-prop-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (120 mg, 58%).

Workup

  1. customprepared
  2. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1 to 7:3 gradient)

Sources & evidence

ORD record
ord-aac2e034cbd04721b28f46fd9d70f6e1
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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