Butanedione → N-(2,2-dimethoxyethyl)-2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine

HRID 1825842노트

반응식

HRID 1825842 반응식
[N:1]1([CH2:6][CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([NH2:17])=[CH:14]3)=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(=O)[C:20](C)=[O:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:38]1[CH2:42][O:41][CH2:40]C1>CCOCC>[CH3:20][O:21][CH:42]([O:41][CH3:40])[CH2:38][NH:17][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][N:8]([CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[N:9]=2)[CH:14]=1

참가 물질

6

반응물 4

HCID 650ButanedioneHCID 8028Tetrahydrofuran2회HCID 5049666Sodium triacetoxyborohydride2회HCID 112069772-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine

생성물 1

HCID 22138916N-(2,2-dimethoxyethyl)-2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine (1.14 g, 0.497 mmol) in 62 mL of dry THF was added 2.04 mL of dimethyl glyoxal in ether (45% glyoxal by weight). A slurry of NaBH(OAc)3 (1.66 g, 7.83 mmol) in THF (10 mL) was slowly added via addition funnel over 60 minutes, and the mixture stirred at room temperature for 12 hours, after which an additional equivalent of NaBH(OAc)3 was added. After an additional 12 hours, the mixture was quenched with saturated NaHCO3, filtered, and the solvents removed under reduced pressure. The residue was purified via column chromatography eluting with 5–15% Et3N in EtOAc to provide 650 mg (2.04 mmol) of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.55–1.73 (m, 4 H) 2.39–2.49 (m, 4 H) 2.85–2.96 (m, 2 H) 3.05–3.20 (m, 2 H) 3.28–3.33 (m, 6 H) 4.31–4.45 (m, 2 H) 4.48–4.61 (m, 1 H) 5.14–5.32 (m, 1 H) 6.37–6.50 (m, 1 H) 6.74–6.91 (m, 1 H) 7.21–7.42 (m, 1 H) 7.83–8.02 (m, 1 H); MS (ESI) m/z 319 [M+H]+.

후처리

  1. waitAfter an additional 12 hours
  2. customthe mixture was quenched with saturated NaHCO3
  3. filtrationfiltered
  4. customthe solvents removed under reduced pressure
  5. customThe residue was purified via column chromatography
  6. washeluting with 5–15% Et3N in EtOAc

출처 및 근거

ORD 기록
ord-ce014252c8e94e4dbd436756db6da13e
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049307B2

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