Water → N7-[(3S)-Tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridine-6,7-diamine

HRID 711930노트

반응식

HRID 711930 반응식
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][O:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].O>C(O)C.[Fe]>[O:16]1[CH2:17][CH2:18][CH2:19][C@H:14]([NH:13][C:5]2[C:4]([NH2:1])=[CH:9][N:8]=[C:7]3[CH:10]=[CH:11][S:12][C:6]=23)[CH2:15]1

참가 물질

6

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 867174126-Nitro-N-[(3S)-tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridin-7-amine

생성물 1

HCID 86717413N7-[(3S)-Tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridine-6,7-diamine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

A mixture of 6-nitro-N-[(3S)-tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridin-7-amine (30 mg, 0.1 mmol), iron (18 mg, 0.32 mmol) and ammonium chloride (29 mg, 0.54 mmol) in ethanol (0.8 mL)/water (0.3 mL) was heated at reflux for 4 h. The resulting mixture was filtered. The filtrate was diluted with EtOAc, washed with sat. NaHCO3 solution, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product. LCMS calculated for C12H16N3OS (M+H)+: m/z=250.1. Found: 250.0.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. filtrationThe resulting mixture was filtered
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with sat. NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-5d1a0e10a5054e99bb14c44cec231122
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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