HCID 16228062, compound → HCID 86624171, compound

HRID 1191127Notes

Reaction equation

HRID 1191127 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]([CH2:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1)[CH:29]([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[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:38][CH2:37][C:36]1[CH:39]=[CH:40][C:33]([CH2:32][N:28]([CH:29]([CH3:31])[CH3:30])[CH3:27])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 16228062HCID 16228062, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86624171HCID 86624171, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (500 mg, 1.18 mmol) with 4-[(N-methyl-iso-propylamino)-methyl]-benzylamine (270 mg, 1.41 mmol) in toluene (10 mL). Purify by chromatography on silica gel (75 g) eluting with a gradient of 100% DCM to 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain 7-chloro-6-{4-[(N-methyl-iso-propylamino)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (350 mg, 64%). MS (APCI) m/z: 468 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel (75 g)
  2. washeluting with a gradient of 100% DCM to 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-961fb99baa784d1bb027129aa8b2272f
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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