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Hydrazine hydrate (1:1) → (+/-)-2-Amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile

HRID 2427274
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인쇄 미리보기

반응식

HRID 2427274 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:33][C:15]2[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=3)[C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][C:22]=3[C:14]=2[CH2:13]1.O.NN>C(O)C.O1CCCC1.C(OCC)(=O)C>[NH2:3][CH:12]1[CH2:33][C:15]2[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=3)[C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][C:22]=3[C:14]=2[CH2:13]1
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참가 물질

6

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 59242740(+/-)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile

생성물 1

HCID 59242745(+/-)-2-Amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile수율 91.5%

시약·촉매·용매 3

HCID 702Ethanol용매
HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

Dissolve (±)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (5.31 g, 12.2 mmol) in ethanol (15 mL)/tetrahydrofuran (85 mL). Add hydrazine monohydrate (4.43 ml, 91.2 mmol, 7.50 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ethyl acetate (150 ml), filter off white solids, wash the organic layer with 10% potassium carbonate twice, dry over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (3.42 g, 91%). LCMS 307.0 (M+1), 305.0 (M−1).

후처리

  1. filtrationfilter off white solids
  2. washwash the organic layer with 10% potassium carbonate twice
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

출처 및 근거

ORD 기록
ord-4e40de03d93642ccb5fb8789daa13aff
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07968587B2

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