Diisopropylamine → 4-(Cyclopropyl-pyridin-4-ylmethyl-amino)-piperidine-1-carboxylic Acid 4-(5-trifluoromethylpyridin-2-yloxy)-phenyl Ester

HRID 1180020Notes

Reaction equation

HRID 1180020 reaction equation
[CH:1]1([N:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=2)=[CH:24][CH:23]=1)=[O:20].C(NC(C)C)(C)C>CN(C)C=O>[F:37][C:35]([F:36])([F:38])[C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:19]([N:15]3[CH2:16][CH2:17][CH:12]([N:4]([CH:1]4[CH2:2][CH2:3]4)[CH2:5][C:6]4[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=4)[CH2:13][CH2:14]3)=[O:20])=[CH:23][CH:24]=2)=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformateHCID 22047949Cyclopropyl-piperidine-4-yl-pyridin-4-ylmethyl-amine

Product 1

HCID 695194424-(Cyclopropyl-pyridin-4-ylmethyl-amino)-piperidine-1-carboxylic Acid 4-(5-trifluoromethylpyridin-2-yloxy)-phenyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title product was prepared from cyclopropyl-piperidine-4-yl-pyridin-4-ylmethyl-amine and 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate, 3 equivalent of diisopropylamine was added, solvent: dimethylformamide. The crude reaction mixture was evaporated without addition of acetic acid, preparative HPLC (method C) (19%, yellow oil). HPLC-MS m/z=(M+1), Rt: 2.82 min.

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. customwas evaporated without addition of acetic acid, preparative HPLC (method C) (19%, yellow oil)

Sources & evidence

ORD record
ord-c8413a7c59394ae4892305f7db9f8a98
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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