Aniline → HCID 66985416, compound

HRID 1616682Notes

Reaction equation

HRID 1616682 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.[NH2:27][C@@H:28]1[CH2:32][CH2:31][C@@H:30]([C:33]([N:35]2[CH2:42][CH2:41][C@:40]3([CH3:46])[C:43]([CH3:45])([CH3:44])[C@H:36]2[CH2:37][C:38]2[C:50]([OH:51])=[CH:49][CH:48]=[CH:47][C:39]=23)=[O:34])[CH2:29]1>ClCCl>[OH:51][C:50]1[C:38]2[CH2:37][C@@H:36]3[C:43]([CH3:44])([CH3:45])[C@:40]([CH3:46])([C:39]=2[CH:47]=[CH:48][CH:49]=1)[CH2:41][CH2:42][N:35]3[C:33]([C@@H:30]1[CH2:31][CH2:32][C@@H:28]([NH:27][C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:25])[CH2:29]1)=[O:34]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 58497679HCID 58497679, compound

Product 1

HCID 66985416HCID 66985416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Aniline (19 μL) and triethylamine (100 μL) dissolved in dichloromethane (0.5 mL) are added to a solution of triphosgene (19 mg) in dichloromethane (0.5 mL) chilled in an ice bath. After stirring the solution for 30 min, [(1R,3R)-3-amino-cyclopentyl]-[(2R,6S)-10-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-methanone (80 mg) and triethylamine (30 μL) dissolved in dichloromethane (1 mL) are added. The resulting solution is stirred in the cooling bath for 15 min and then at room temperature for 2 h. The solution is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H) to give the title compound.

Workup

  1. temperaturechilled in an ice bath
  2. additionare added
  3. stirringThe resulting solution is stirred in the cooling bath for 15 min
  4. waitat room temperature for 2 h
  5. concentrationThe solution is concentrated under reduced pressure
  6. customthe residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H)

Sources & evidence

ORD record
ord-5c916b2ce2fd430fb8d61f48be159d77
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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