Phenyl isocyanate → HCID 86629598, compound

HRID 911230Notes

Reaction equation

HRID 911230 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH2:12][O:13][C:14]1[C:24]2[CH2:23][CH2:22][N:21]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:20][CH2:19][C:18]=2[CH:17]=[CH:16][C:15]=1[Cl:31]>C(Cl)Cl>[Cl:31][C:15]1[CH:16]=[CH:17][C:18]2[CH2:19][CH2:20][N:21]([C:25](=[O:30])[C:26]([F:28])([F:27])[F:29])[CH2:22][CH2:23][C:24]=2[C:14]=1[O:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 57655967HCID 57655967, compound

Product 1

HCID 86629598HCID 86629598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine phenyl isocyanate (16.3 mg, 0.137 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. 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 7-chloro-6-[2-(3-phenyl-ureido)-ethoxy]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine.

Workup

  1. concentrationConcentrate in vacuo
  2. 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-84d476a069754035ac0c2729cbb1fcd4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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