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

HRID 711930ノート

反応式

HRID 711930 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5d1a0e10a5054e99bb14c44cec231122
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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