Diisopropylethylamine → HCID 86710227, compound

HRID 2405909Notes

Reaction equation

HRID 2405909 reaction equation
[C: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][CH: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>[C: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)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 70817544HCID 70817544, compound

Product 1

HCID 86710227HCID 86710227, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-4-[4-(cyclohex-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (339 mg, 1.04 mmol, 1.0 eq) in dichloromethane (10 mL) under nitrogen, was added DIPEA (285 mg, 2.20 mmol, 0.384 mL, 2.12 eq) followed by the addition of 1-hydroxybenzotriazole monohydrate (307 mg, 2.00 mmol, 1.93 eq). The solution was allowed to stir for 30 minutes before being treated with O-tetrahydro-2H-pyran-2-yl-hydroxylamine (163 mg, 1.39 mmol, 1.34 eq) and then dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (285 mg 1.49 mmol, 1.43 eq). The mixture was then allowed to stir for 3 hours at RT. The mixture was then absorbed onto silica gel and purified by flash chromatography eluting with 5-100% EtOAc/Hpt to give (2R)-4-[4-(cyclohex-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (230 mg, 52% yield). LC-MS M+H+426.1.

Workup

  1. stirringto stir for 3 hours at RT
  2. customThe mixture was then absorbed onto silica gel
  3. custompurified by flash chromatography
  4. washeluting with 5-100% EtOAc/Hpt

Sources & evidence

ORD record
ord-9392b6f157854e0790e8118b01e45a68
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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