7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 7-chloro-6-[(6-iso-propoxymethyl-pyridin-3-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1191120Notes

Reaction equation

HRID 1191120 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.[NH2:27][CH2:28][C:29]1[CH:30]=[N:31][C:32]([CH2:35][O:36][CH:37]([CH3:39])[CH3:38])=[CH:33][CH:34]=1>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:27][CH2:28][C:29]1[CH:30]=[N:31][C:32]([CH2:35][O:36][CH:37]([CH3:39])[CH3:38])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 584955003-Aminomethyl-6-(iso-propoxy)methyl-pyridine

Product 1

HCID 866241657-chloro-6-[(6-iso-propoxymethyl-pyridin-3-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

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 (408 mg, 0.96 mmol) with 3-aminomethyl-6-(iso-propoxy)methyl-pyridine (190 mg, 1.05 mmol) in toluene (8 mL). Purify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 1:1 gradient) to obtain 7-chloro-6-[(6-iso-propoxymethyl-pyridin-3-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine. MS (ES+) m/z: 456 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b3357c37d4f44770b72d8c75cbf4ded5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…