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Hydrochloric Acid → 5-{4-[2-(methylthio)pyrimidin-4-yl]-1H-pyrazol-3-yl}-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 500740
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HRID 500740 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[C:23]([C:24]5[CH:29]=[CH:28][N:27]=[C:26]([S:30][CH3:31])[N:25]=5)=[CH:22][N:21](C5CCCCO5)[N:20]=4)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.P([O-])([O-])([O-])=O>CO.O1CCOCC1>[CH3:31][S:30][C:26]1[N:25]=[C:24]([C:23]2[C:19]([C:17]3[CH:18]=[C:13]4[CH:12]=[CH:11][N:10]([S:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)(=[O:8])=[O:9])[C:14]4=[N:15][CH:16]=3)=[N:20][NH:21][CH:22]=2)[CH:29]=[CH:28][N:27]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 57856232HCID 57856232, 화합물

생성물 1

HCID 1785034265-{4-[2-(methylthio)pyrimidin-4-yl]-1H-pyrazol-3-yl}-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine수율 98.4%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 31275
1,4-Dioxane
용매

실험 절차

To a solution of the 1-Benzenesulfonyl-5-[4-(2-methylsulfanyl-pyrimidin-4-yl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (C-1-2) (750 mg, 1.41 mmol) in MeOH (1 mL) was added a solution of HCl in Dioxane (˜4N, 0.1 mL). After stirring at ambient temperature for 45 minutes, the solution was dropped into phosphate buffer (pH 7, 15 mL). The resulting precipitate was collected by filtration, rinsed with water and air dried to give 5-{4-[2-(methylthio)pyrimidin-4-yl]-1H-pyrazol-3-yl}-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (C-1-3) (622 mg, 98%) which was carried on without further purification. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 11.51 (br. s., 1H), 8.47 (d, J=2.02 Hz, 1H), 8.34 (d, J=5.05 Hz, 1H), 8.23 (br. s., 1H), 8.14 (d, J=7.58 Hz, 2H), 8.10 (d, J=1.77 Hz, 1H), 7.84 (d, J=2.78 Hz, 1H), 7.68 (t, J=7.45 Hz, 1H), 7.57 (t, J=7.71 Hz, 2H), 7.07 (d, J=4.80 Hz, 1H), 6.75 (d, J=3.79 Hz, 1H), 1.81 (s, 3H).

후처리

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with water and air
  3. customdried

출처 및 근거

ORD 기록
ord-5b3e68c19fe84b83859ca8f2936b141e
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772246B2

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