Phenol → HCID 69526139, compound

HRID 1831367Notes

Reaction equation

HRID 1831367 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)=[CH:19][CH:18]=1)=[O:15].C1(O)C=CC=CC=1>ClCCl>[F:32][C:30]([F:31])([F:33])[C:27]1[CH:28]=[CH:29][C:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:14]([N:10]3[CH2:11][CH2:12][CH:7]([CH2:6][NH:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH2:8][CH2:9]3)=[O:15])=[CH:18][CH:19]=2)=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 22047753HCID 22047753, compoundHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformate

Product 1

HCID 69526139HCID 69526139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopropylmethyl-piperidine-4-ylmethyl-amine (0.65 mmol, 110 mg) was dissolve in dichloromethane. 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate (0.65 mmol, 0.208 g) (prepared from the corresponding phenol by conventional methods) was added at −15° C. for 15 min and stired at room temperature overnight and evaporated to dryness. The crude product was purified by preparative HPLC (Method C) (16%, colourless crystals). HPLC-MS m/z=450.1 (M+1), Rt: 2.98 min.

Workup

  1. additionwas added at −15° C. for 15 min
  2. customevaporated to dryness
  3. customThe crude product was purified by preparative HPLC (Method C) (16%, colourless crystals)

Sources & evidence

ORD record
ord-a8455b90228d4d3a9c374757a70692d2
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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