HCID 86717569, compound → HCID 86717570, compound

HRID 712118Notes

Reaction equation

HRID 712118 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:10][CH2:9][C@@H:8]([N:11]2[C:15]3=[C:16]4[S:22][CH:21]=[CH:20][C:17]4=[N:18][CH:19]=[C:14]3[N:13]=[C:12]2[C@H:23]([OH:25])[CH3:24])[CH2:7][CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]1[O:10][CH2:9][C@@H:8]([N:11]2[C:15]3=[C:16]4[S:22][CH:21]=[CH:20][C:17]4=[N:18][CH:19]=[C:14]3[N:13]=[C:12]2[C@H:23]([OH:25])[CH3:24])[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 86717569HCID 86717569, compound

Product 1

HCID 86717570HCID 86717570, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1R)-1-{1-[(3S,6R)-6-(azidomethyl)tetrahydro-2H-pyran-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol (12 mg, 0.034 mmol) in methanol (0.2 mL) was added 10% palladium on carbon (5.7 mg). The resulting mixture was stirred under H2 balloon overnight. The reaction mixture was filtered through a pad of Celite and washed with methanol. The solvent was removed under reduced pressure to give the desired product (11 mg, 99%). LCMS calculated for C16H21N4O2S (M+H)+: m/z=333.1. Found: 333.1.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4255d9b1036641c6ad74fa40c2421218
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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