HCID 591671, compound → HCID 86629688, compound

HRID 911694Notes

Reaction equation

HRID 911694 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.[CH2:27]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][C:31]=1[Cl:38])[CH3:28]>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:35][CH2:34][C:33]1[CH:36]=[CH:37][C:30]([O:29][CH2:27][CH3:28])=[C:31]([Cl:38])[CH:32]=1

Participants

4

Reactant 2

HCID 591671HCID 591671, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629688HCID 86629688, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Use a method similar to the General Procedure 5-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg, 0.35 mmol) with 4-ethoxy-3-chloro-benzylamine (94.7 mg, 0.51 mmol) in anhydrous 1,4-dioxane (10 mL). Purify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (100:0 to 77:23 gradient) to obtain 7-chloro-6-(3-chloro-4-ethoxy-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (111.3 mg, 68%). MS (ES+) m/z: 483 (M+Na)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (100:0 to 77:23 gradient)

Sources & evidence

ORD record
ord-93c38103991a412b97c2063fb57aead3
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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