HCID 16776699, compound → HCID 86624172, compound

HRID 1191130Notes

Reaction equation

HRID 1191130 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]([CH3:41])([CH3:40])[C:29]([NH:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1)=[O:30]>C1(C)C=CC=CC=1.O1CCOCC1>[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[NH:37][CH2:36][C:35]1[CH:34]=[CH:33][C:32]([NH:31][C:29](=[O:30])[C:28]([CH3:40])([CH3:27])[CH3:41])=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 16776699HCID 16776699, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86624172HCID 86624172, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 21840791Dioxane tolueneSolvent

Procedure

Use a method similar to the General Procedure 1-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.33 g, 0.78 mmol) with a solution of 4-(2,2-dimethyl-propionylamino)-benzylamine (0.32 g, 1.6 mmol) in anhydrous toluene/dioxane (4:1, 10 mL). Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 7:3 gradient over 30 min; 35 mL/min) and then by SCX chromatography to obtain 7-chloro-6-[4-(2,2-dimethyl-propionylamino)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (0.266 g, 70%). MS (ES+) m/z: 482 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 7:3 gradient over 30 min; 35 mL/min)

Sources & evidence

ORD record
ord-956f8f6cb0c044bb80c8d095e24bf821
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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