Triethylamine → HCID 67417210, compound

HRID 1770388Notes

Reaction equation

HRID 1770388 reaction equation
[F:1][CH:2]([F:37])[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[S:21][CH:22]=[C:23]([C:25]4[CH2:29][CH:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[OH:36])[O:27][N:26]=4)[N:24]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.C(N(CC)CC)C.[CH:45]1([C:51](Cl)=[O:52])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>C(Cl)Cl>[CH:45]1([C:51]([O:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH:28]2[O:27][N:26]=[C:25]([C:23]3[N:24]=[C:20]([CH:17]4[CH2:16][CH2:15][N:14]([C:12](=[O:13])[CH2:11][N:5]5[C:6]([CH:8]([F:10])[F:9])=[CH:7][C:3]([CH:2]([F:1])[F:37])=[N:4]5)[CH2:19][CH2:18]4)[S:21][CH:22]=3)[CH2:29]2)=[O:52])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 665846872-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

Product 1

HCID 67417210HCID 67417210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (150 mg) and triethylamine (33 mg) in methylene chloride (10 ml) is added, at 0° C., a solution of cyclohexanecarbonyl chloride in methylene chloride (2 ml). The ice bath is removed and the reaction mixture is stirred at 0° C.-RT for 3 h. Then the mixture is admixed with dilute sodium hydrogencarbonate solution and extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated. Purification by column chromatography gives 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl cyclohexanecarboxylate (150 mg).

Workup

  1. customThe ice bath is removed
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-97cb931e8a6a4683acf7e252b0fb383a
Source dataset
uspto-grants-2016_02
Patent number
US09247748B2

Reaction notes

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