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

HRID 711930Notes

Reaction equation

HRID 711930 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5d1a0e10a5054e99bb14c44cec231122
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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