Hydrochloric Acid → HCID 58546712, 화합물

HRID 1850326노트

반응식

[CH3:1][N:2]([CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([CH:21]3[CH2:24][N:23]([C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[CH2:22]3)=[N:19][CH:18]=[CH:17][N:16]=2)[CH2:11]1)C(=O)OC(C)(C)C.Cl.C(O)(C)C>>[CH3:1][NH:2][CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([CH:21]3[CH2:24][N:23]([C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[CH2:22]3)=[N:19][CH:18]=[CH:17][N:16]=2)[CH2:11]1

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 3776Isopropanol

HCID 58547135HCID 58547135, 화합물

생성물 1

HCID 58546712HCID 58546712, 화합물수율 44.1%

실험 절차

To a round bottomed flask was added tert-butyl methyl(1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-yl)carbamate (3.0 g, 6.51 mmol) and hydrogen chloride, 5-6N in isopropanol (0.237 g, 6.51 mmol) to stir overnight. Solvent was evaporated and the reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, saturated Na2CO3, saturated NaCl, and dried over MgSO4, filtered and concentrated in vacuo to give N-methyl-1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-amine (1.0339 g, 2.87 mmol, 44.0% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.71-1.83 (m, 1H) 2.02 (dt, J=12.18, 5.94 Hz, 1H) 2.32 (s, 2H) 3.16-3.28 (m, 1H) 3.32 (br. s., 1H) 3.42-3.52 (m, 1H) 3.54-3.67 (m, 1H) 4.29-4.45 (m, 4H) 6.78 (d, J=8.80 Hz, 1H) 7.17-7.25 (m, 1H) 7.48-7.59 (m, 2H) 7.71 (d, J=7.83 Hz, 1H) 7.91 (d, J=2.54 Hz, 1H) 7.97 (d, J=2.35 Hz, 1H) 8.03 (d, J=8.80 Hz, 1H)

후처리

customSolvent was evaporated
additionthe reaction mixture was diluted with water
extractionextracted with EtOAc
extractionThe organic extract
washwas washed with water, saturated Na2CO3, saturated NaCl
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

출처 및 근거

ORD 기록: ord-066c37afce48412ca47c45d842deb05f
출처 데이터셋: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08957073B2

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