Hydrochloric Acid → HCID 86629600, compound

HRID 911352Notes

Reaction equation

HRID 911352 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:15]2[CH2:14][CH2:13][N:12]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[Cl:22].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[C:23]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[C:15]2[CH2:14][CH2:13][N:12]([C:16](=[O:21])[C:17]([F:19])([F:18])[F:20])[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[Cl:22])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57656463HCID 57656463, compound

Product 1

HCID 86629600HCID 86629600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 6-(2-amino-ethylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (70 mg, 0.208 mmol) in DCM (4 mL). Add benzoyl chloride (24 μL, 0.208 mmol), and triethylamine (44 μL, 0.312 mmol) and stir at ambient temperature for 24 h under nitrogen atmosphere. Dilute with DCM and add 1M aqueous HCl. Extract the aqueous layer with DCM. Dry the organic layer over MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 7:3 and 1:1) to obtain 6-(2-benzoylamino-ethylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine.

Workup

  1. extractionExtract the aqueous layer with DCM
  2. dry with materialDry the organic layer over MgSO4
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 7:3 and 1:1)

Sources & evidence

ORD record
ord-4d691cd43bd44008a5c4a4ddf64997bc
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…