Triethylamine → HCID 59432474, compound

HRID 507142Notes

Reaction equation

HRID 507142 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.[CH:25]([O:28][C:29]([N:31]1[CH2:37][CH2:36][CH2:35][CH:34]([NH:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:45]=[C:46]([CH3:53])[C:47]([C:49]([F:52])([F:51])[F:50])=[CH:48][C:32]1=2)=[O:30])([CH3:27])[CH3:26]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:25]([O:28][C:29]([N:31]1[CH2:37][CH2:36][CH2:35][CH:34]([N:38]([C:6](=[O:7])[C:5]2[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)[C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:45]=[C:46]([CH3:53])[C:47]([C:49]([F:51])([F:52])[F:50])=[CH:48][C:32]1=2)=[O:30])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 59432423HCID 59432423, compound

Product 1

HCID 59432474HCID 59432474, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Add 3,5-bis(trifluoromethyl)-benzoyl chloride (0.220 mL, 1.22 mmol) and triethylamine (0.180 mL, 1.29 mmol) over a 24 h period to a solution of 7-methyl-5-(pyridin-3-ylamino)-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester (114 mg, 0.280 mmol) in chloroform (1.9 mL) at 70° C. Allow the reaction to cool, dilute with methylene chloride (20 mL) and wash sequentially with 10% HCl, saturated aqueous sodium bicarbonate, water, and then brine. Dry (MgSO4), concentrate, and purify via column chromatography (silica gel; 20% to 40% EtOAc:hexanes) to give 92 mg (51%) of the title compound as a white solid APCI MS m/z 648 [M+H]+.

Workup

  1. customthe reaction
  2. temperatureto cool
  3. washwash sequentially with 10% HCl, saturated aqueous sodium bicarbonate, water
  4. dry with materialDry (MgSO4)
  5. concentrationconcentrate
  6. custompurify via column chromatography (silica gel; 20% to 40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-345fb1231f7e4ff59ba10824b44507d9
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…