Benzoyl chloride → HCID 86629595, compound

HRID 911226Notes

Reaction equation

HRID 911226 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCOCC1.[NH2:16][CH2:17][CH2:18][O:19][C:20]1[C:30]2[CH2:29][CH2:28][N:27]([C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])[CH2:26][CH2:25][C:24]=2[CH:23]=[CH:22][C:21]=1[Cl:37]>C(Cl)Cl>[C:1]([NH:16][CH2:17][CH2:18][O:19][C:20]1[C:30]2[CH2:29][CH2:28][N:27]([C:31](=[O:36])[C:32]([F:33])([F:35])[F:34])[CH2:26][CH2:25][C:24]=2[CH:23]=[CH:22][C:21]=1[Cl:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8083MorpholineHCID 57655967HCID 57655967, compound

Product 1

HCID 86629595HCID 86629595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine benzoyl chloride (19.3 mg, 0.137 mmol), PS-morpholine (109 mg, 0.272 mmol), 6-(2-amino-ethoxy)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (46 mg, 0.137 mmol) in DCM (1.5 mL) and stir at ambient temperature for 16 h. Filter the resin, wash with DCM and concentrate in vacuo. Purify by reverse phase HPLC (10-95% of solvent B in 12.8 min, 25 mL/min; solvent A: water, 0.1% trifluoroacetic acid; solvent B: acetonitrile, 0.1% trifluoroacetic acid; column: YMC SH-341-5, S-5 μm, 12 nm, 100×20 mm) to give 6-(2-benzoylamino-ethoxy)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine.

Workup

  1. filtrationFilter the resin
  2. washwash with DCM
  3. concentrationconcentrate in vacuo
  4. customPurify by reverse phase HPLC (10-95% of solvent B in 12.8 min, 25 mL/min; solvent A: water, 0.1% trifluoroacetic acid; solvent B: acetonitrile, 0.1% trifluoroacetic acid; column: YMC SH-341-5, S-5 μm, 12 nm, 100×20 mm)

Sources & evidence

ORD record
ord-5b83e56eb49d4c66a161897e6b5ef31e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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