Water → HCID 66687047, compound

HRID 1910984Notes

Reaction equation

HRID 1910984 reaction equation
[F:1][CH:2]([F:29])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.[CH:30]1(O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N=C=NCCCN(C)C)C.O>ClCCl.CN(C)C1C=CN=CC=1>[F:29][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:9])[F:10])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:25]=[C:24]([C:26]([O:28][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:27])[CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7966CyclohexanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66686823HCID 66686823, compound

Product 1

HCID 66687047HCID 66687047, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-pyridine-2-carboxylic acid (157 mg) in dichloromethane (5 ml) are added, at room temperature, cyclohexanol (42 mg), 4-dimethylaminopyridine (4.6 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (80 mg). The mixture is stirred at room temperature overnight, and then water is added. The aqueous phase is removed and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography. This gives cyclohexyl 6-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)pyridine-2-carboxylate (87 mg).

Workup

  1. customThe aqueous phase is removed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-17af87e1a4004df684702346e4fc5e02
Source dataset
uspto-grants-2013_12
Patent number
US08604040B2

Reaction notes

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