Water → N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

HRID 852457Notes

Reaction equation

HRID 852457 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15](Cl)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:20]1([CH2:26][N:27]2[CH2:32][CH:31]=[C:30]([C:33]3[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl.C(N(CC)CC)C>[C:20]1([CH2:26][N:27]2[CH2:28][CH:29]=[C:30]([C:33]3[CH:34]=[CH:35][C:36]([NH:39][C:15]([C:10]4[C:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=5)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:16])=[CH:37][CH:38]=3)[CH2:31][CH2:32]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chlorideHCID 224994164-[1,2,3,6-Tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine

Product 1

HCID 22499387N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideYield 88.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4′-(Trifluoromethyl)-[1,1′-biphenyl]-2-carbonyl chloride (0.12 mol) was added dropwise to a stirring mixture of 4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine (0.095 mol) in DCM (300 ml) and triethylamine (50 ml). The mixture was stirred overnight, poured out into water and then stirred for 30 minutes. The organic layer was separated, washed, dried, filtered and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 43 g of N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 20).

Workup

  1. stirringstirred for 30 minutes
  2. customThe organic layer was separated
  3. washwashed
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was triturated in DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-8c848146c7ee4180a1277fade4c5ab06
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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