Diisopropylethylamine → HCID 59852617, compound

HRID 2373806Notes

Reaction equation

HRID 2373806 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:9]=1[O:10]C(=O)C)=[O:3].Cl.[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][C@@H:42]([NH2:49])[C:43]3[O:47][N:46]=[C:45]([CH3:48])[N:44]=3)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27].CCN(C(C)C)C(C)C>>[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][C@@H:42]([NH:49][C:9]([C:4]3[CH:5]=[C:6]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=4)[CH:7]=[CH:8][C:2]=3[OH:3])=[O:10])[C:43]3[O:47][N:46]=[C:45]([CH3:48])[N:44]=3)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 69207199HCID 69207199, compoundHCID 86032175HCID 86032175, compound

Product 1

HCID 59852617HCID 59852617, compound

Procedure

4-Hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2(4′-methanesulfonyl-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (49 mg) was prepared from acetic acid 3-chlorocarbonyl-4′-trifluoromethyl-biphenyl-4-yl ester (1.93 mL, 0.1 M CH2Cl2) and 2-(4′-methanesulfonyl-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethylamine hydrochloride (80 mg, 0.175 mmol) and DIEA (92 μL, 0.525 mmol) using standard procedure M. The crude reaction mixture was concentrated and redissolved in THF (3 mL) and MeOH (1 mL). 1 N NaHCO3 (200 μL) and 1N Na2CO3 (50 μL) were added and the hydrolysis was followed by TLC and LCMS. Once complete, the reaction was diluted with EtOAc and the layers were separated. After extraction and drying the combined organics over MgSO4, the crude mixture was concentrated onto silica gel and purified by chromatography using 15% EtOAc in hexanes.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. dissolutionredissolved in THF (3 mL)
  4. addition1 N NaHCO3 (200 μL) and 1N Na2CO3 (50 μL) were added
  5. additionOnce complete, the reaction was diluted with EtOAc
  6. customthe layers were separated
  7. extractionAfter extraction
  8. dry with materialdrying the combined organics over MgSO4
  9. concentrationthe crude mixture was concentrated onto silica gel
  10. custompurified by chromatography

Sources & evidence

ORD record
ord-99ca9e92e5084dee96143c6481291d11
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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