Triethylamine → N-[1-(1,5-dimethyl-1H-pyrazol-4-yl)ethyl]-6-(1-hydroxy-1-methylethyl)-2-naphthamide

HRID 2425576노트

반응식

HRID 2425576 반응식
[OH:1][C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=O)[CH:9]=[CH:8]2)([CH3:4])[CH3:3].Cl.Cl.[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([C@H:27]([NH2:29])[CH3:28])[CH:23]=[N:22]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([CH:27]([NH:29][C:15]([C:10]2[CH:9]=[CH:8][C:7]3[C:12](=[CH:13][CH:14]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[CH:6]=3)[CH:11]=2)=[O:17])[CH3:28])[CH:23]=[N:22]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 137823686-(2-Hydroxy-2-propyl)naphthalene-2-carboxylic acidHCID 67180429HCID 67180429, 화합물

생성물 1

HCID 24947119N-[1-(1,5-dimethyl-1H-pyrazol-4-yl)ethyl]-6-(1-hydroxy-1-methylethyl)-2-naphthamide수율 58.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a DMF (3 ml) solution of 6-(1-Hydroxy-1-methyl-ethyl)-naphthalene-2-carboxylic acid (U.S. Pat. No. 4,638,087, published 20 Jan. 1987, 95 mg, 0.413 mmol), Amine 9 (1-(5-Methyl-1H-pyrazol-4-yl)ethanamine dihydrochloride, 95 mg, 0.352 mmol), HBTU (188 mg, 0.495 mmol) and triethylamine (0.173 ml, 1.24 mmol) were added and the mixture was stirred for 24 hours at room temperature. The reaction was quenched with sat. NaHCO3 aq and water, and the product extracted with EtOAc 3 times. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (Ethylacetate:Hexane=2:1) to give the title product as a white solid (84.4 mg, 58.2% yield). 1H NMR (300 MHz, DMSO-d6) δ 1.46-1.49 (3H, d), 1.50-1.53 (6H, s) 2.22-2.24 (3H, s) 3.67-3.68 (3H s) 5.13-5.20 (2H, m) 7.38-7.39 (1H, s) 7.69-7.72 (1H, d) 7.81-8.00 (4H, m) 8.39-8.40 (1H, s) 8.68-8.72 (1H, d). MS (ESI) m/z 352 (M+H)+.

후처리

  1. customThe reaction was quenched with sat. NaHCO3 aq and water
  2. extractionthe product extracted with EtOAc 3 times
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel column chromatography (Ethylacetate:Hexane=2:1)

출처 및 근거

ORD 기록
ord-c8b6407c872249a89a1cf6cf9f6aaefe
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964732B2

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