Water → 1,2,3,4-Tetrahydronaphthalen-1-yl 6-(4-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-acetyl}piperazin-1-yl)pyridine-2-carboxylate

HRID 403207

Reaction equation

HRID 403207 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][N: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)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[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[CH2:15][CH2:16][N:17]([C:20]3[N:25]=[C:24]([C:26]([O:28][CH:38]4[C:39]5[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:35][CH2:36][CH2:37]4)=[O:27])[CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]2)=[O:13])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 666867066-(4-{[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)pyridine-2-carboxylic acid

Product 1

HCID 666867931,2,3,4-Tetrahydronaphthalen-1-yl 6-(4-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-acetyl}piperazin-1-yl)pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(4-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)-pyridine-2-carboxylic acid (150 mg) in dichloromethane (5 ml) are added, at room temperature, 1,2,3,4-tetrahydronaphthalen-1-ol (70 mg), 4-dimethylaminopyridine (4.4 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (104 mg). The mixture is stirred at room temperature overnight, and then water is added. The aqueous phase is removed and extracted with ethyl acetate, and then the combined organic phases are dried over sodium sulphate. The solids are filtered off and the solvent is distilled off. The residue is purified by chromatography. This gives 1,2,3,4-tetrahydronaphthalen-1-yl 6-(4-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)pyridine-2-carboxylate (70 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. filtrationThe solids are filtered off
  5. distillationthe solvent is distilled off
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-07497e7023b2438589779f0d536686f5
Source dataset
uspto-grants-2014_06
Patent number
US08748420B2

Linked notes

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