Triethylamine → HCID 86589089, compound

HRID 1168867Notes

Reaction equation

HRID 1168867 reaction equation
[CH2:1]([N:3]([CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH:4]1[CH2:13][C:12]2[CH:11]=[C:10]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5]1)[CH3:2].C(N(CC)CC)C.[CH:35]([N:38]=[C:39]=[O:40])([CH3:37])[CH3:36]>C(Cl)Cl>[CH:35]([NH:38][C:39]([N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][N:3]([CH2:1][CH3:2])[CH:4]2[CH2:5][CH2:6][C:7]3[C:12](=[CH:11][C:10]([NH:14][C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])=[CH:9][CH:8]=3)[CH2:13]2)[CH2:27][CH2:26]1)=[O:40])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 22560629HCID 22560629, compound

Product 1

HCID 86589089HCID 86589089, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-2,2,2-trifluoro-acetamide (1.7 mmol) in methylene chloride (20 mL) under an inert atmosphere was added triethylamine (1.0 mL, 6.6 mmol) and isopropyl isocyanate (230 μL, 2.3 mmol). The reaction was stirred for 20 h and then concentrated in vacuo. This material was partitioned between 5% KOH and water. The organic layer was dried (MgSO4) and concentrated to afford 4-({ethyl-[7-(2,2,2-trifluoro-acetylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid isopropylamide as a clear oil (630 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThis material was partitioned between 5% KOH and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-08aea09f463c4b39ae12e53039edaafd
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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