1-Hydroxybenzotriazole → 2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide

HRID 1881814노트

반응식

HRID 1881814 반응식
Cl.[CH3:2][O:3][NH:4][CH3:5].[CH:6]1([S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:19](O)=[O:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:8][CH2:7]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:6]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:19]([N:4]([O:3][CH3:2])[CH3:5])=[O:20])=[CH:16][CH:17]=2)(=[O:10])=[O:11])[CH2:8][CH2:7]1

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103150842-(4-(Cyclopropylsulfonyl)phenyl)-3-(tetrahydro-2H-pyran-4-YL)propanoic acid

생성물 1

HCID 593315972-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide수율 81%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-methoxymethanamine hydrochloride (3.90 g) in N,N-dimethylformamide (100 mL) was added triethylamine (5.60 mL) for neutralization, and a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propanoic acid (11.23 g) in N,N-dimethylformamide (50 mL), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (9.60 g) and 1-hydroxybenzotriazole (6.80 g) were added under ice-cooling. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, and washed with water, 1N aqueous hydrochloric acid solution and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (10.2 g, yield 81%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 382 (MH+).

후처리

  1. temperaturecooling
  2. washwashed with water, 1N aqueous hydrochloric acid solution and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-145306b2032c425ab589b4913a497362
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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