Diisopropylethylamine → HCID 86710230, compound

HRID 2405912Notes

Reaction equation

HRID 2405912 reaction equation
[CH:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:15]([OH:17])=O)[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.O.ON1C2C=CC=CC=2N=N1.[O:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]1[O:49][NH2:50].Cl.CN(CCCN=C=NCC)C>ClCCl>[CH:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:15]([NH:50][O:49][CH:44]3[CH2:45][CH2:46][CH2:47][CH2:48][O:43]3)=[O:17])[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 70817727HCID 70817727, compound

Product 1

HCID 86710230HCID 86710230, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (30 mg, 0.091 mmol, 1 eq) in dichloromethane (5 mL) under nitrogen, was added DIPEA (24.9 mg, 0.193 mmol, 0.0340 mL, 2.12 eq) followed by 1-hydroxybenzotriazole monohydrate (27.0 mg, 0.176 mmol, 1.93 eq). The solution was allowed to stir for 30 minutes before being treated with O-tetrahydro-2H-pyran-2-yl-hydroxylamine (14.3 mg, 0.122 mmol, 1.34 eq) and then dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (24.9 mg, 0.130 mmol, 1.43 eq). The mixture was then allowed to stir for 3 hours at RT. The reaction mixture was then adsorbed onto silica gel and purified by flash chromatography eluting with 5-100% EtOAc/Hpt to give (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (8.8 mg, 23% yield). LC-MS M+H+428.1.

Workup

  1. stirringto stir for 3 hours at RT
  2. custompurified by flash chromatography
  3. washeluting with 5-100% EtOAc/Hpt

Sources & evidence

ORD record
ord-5c7a32c5ca734147b879f07d5cff8cf5
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

Loading…