HCID 30046248, compound → HCID 86624173, compound

HRID 1191131Notes

Reaction equation

HRID 1191131 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@@H:28]1[CH2:30][C@H:29]1[C:31]([NH:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1)=[O:32]>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:39][CH2:38][C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:31]([C@@H:29]2[CH2:30][C@H:28]2[CH3:27])=[O:32])=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 30046248HCID 30046248, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86624173HCID 86624173, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

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 (0.94 g, 2.2 mmol) with a solution of (±)-trans-4-[(2-methyl-cyclopropanecarbonyl)-amino]-benzylamine (0.899 g, 4.403 mmol) in anhydrous toluene (22 mL) and anhydrous dioxane (5.8 mL). Purify by chromatography on silica gel to afford (±)-trans-7-chloro-6-{4-[(2-methyl-cyclopropanecarbonyl)-amino]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine (0.834 g, 79%) as an orange oil.

Workup

  1. customPurify by chromatography on silica gel

Sources & evidence

ORD record
ord-9b0e0ed24dec4939af1bc9900ad03a6a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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