HCID 28755594, compound → HCID 86624174, compound

HRID 1191132Notes

Reaction equation

HRID 1191132 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][N:28]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>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:34][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([N:28]([C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])[CH3:27])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 28755594HCID 28755594, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86624174HCID 86624174, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21840791Dioxane tolueneSolvent

Procedure

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.23 g, 0.53 mmol) with a solution of 4-(N-methyl-2,2-dimethyl-propionylamino)-benzylamine (0.23 g, 1.06 mmol) in anhydrous toluene/dioxane (4:1, 7 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 17:3 gradient over 30 min, 17:3 over 30 min, 17:3 to 7:3 gradient over 30 min and 7:3 over 30 min; 35 mL/min) to obtain 7-chloro-6-[4-(N-methyl-2,2-dimethyl-propionylamino)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine as a yellow oil (0.235 g, 90%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 17:3 gradient over 30 min, 17:3 over 30 min, 17:3 to 7:3 gradient over 30 min and 7:3 over 30 min; 35 mL/min)

Sources & evidence

ORD record
ord-18b48c7638fa42458dc82eaa0ce9274a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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