Water → HCID 67500537, compound

HRID 1428362Notes

Reaction equation

HRID 1428362 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH2:16][OH:17])[C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][S:11][CH3:12])=[CH:5][N:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].O>ClCCl.CN(C)C1C=CN=CC=1>[C:31]([O:17][CH2:16][CH2:15][N:7]([C:6]1[C:2]([Cl:1])=[N:3][N:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=1)[C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][S:11][CH3:12])(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67500397HCID 67500397, compound

Product 1

HCID 67500537HCID 67500537, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-(2-hydroxyethyl)-2-methyl-3-(methylthio)propanamide (0.045 g, 0.127 mmol) in dichloromethane (1.27 ml) was added N,N-dimethylpyridin-4-amine (0.023 g, 0.190 mmol) and triethylamine (0.019 g, 0.190 mmol) followed by acetyl chloride (0.015 g, 0.190 mmol). The reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with dichloromethane. The combined organic phases were concentrated and chromatographed (0-100% ethyl acetate/hexanes) to give 2-(N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-methyl-3-(methylthio)propanamido)ethyl acetate as a yellow oil (0.015 g, 0.034 mmol, 26.8%): IR (thin film) 1739, 1669 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.97 (d, J=2.3 Hz, 1H), 8.64 (dd, J=4.7, 1.4 Hz, 1H), 8.15 (s, 1H), 8.04 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.47 (ddd, J=8.3, 4.8, 0.7 Hz, 1H), 4.50-3.40 (m, 4H), 2.84 (dd, J=12.7, 8.9 Hz, 1H), 2.78-2.63 (m, 1H), 2.46 (dd, J=12.7, 5.4 Hz, 1H), 2.03 (s, 3H), 2.01 (s, 3H), 1.16 (d, J=6.6 Hz, 3H); ESIMS m/z 398 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. concentrationThe combined organic phases were concentrated
  3. customchromatographed (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2782849829f74178855fb8d7d9a68bc8
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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