Triethylamine → 1-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 468123노트

반응식

HRID 468123 반응식
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6]2)[CH2:2]1.[C:17]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([Br:30])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]1[C:31](O)=[O:32])(=[O:19])[CH3:18].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:17]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([Br:30])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]1[C:31]([N:1]1[CH2:2][CH:3]([N:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])[CH2:9][CH2:10]2)[CH2:4]1)=[O:32])(=[O:19])[CH3:18]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 596256781-(4-Azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanoneHCID 596259471-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

생성물 1

HCID 596259251-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline수율 69.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of compound 1g (228 mg, 0.74 mmol), compound 25c (22 mg, 0.74 mmol), and Et3N (0.3 mL, 2.22 mmol) in CH2Cl2 (7 mL) was added HATU (338 mg, 0.89 mmol). The reaction mixture was stirred at room temperature for 18 h. The resultant mixture was diluted with CH2Cl2 and washed with aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc+0.5% Et3N) gave compound 25d (265 mg). LC/MS m/z (M+H+), 517.0 (M+2H+), 519.0.

후처리

  1. washwashed with aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc+0.5% Et3N)

출처 및 근거

ORD 기록
ord-5a55bb59a960427d8f3cef6e8694c615
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623858B2

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