Water → HCID 73774917, compound

HRID 712113Notes

Reaction equation

HRID 712113 reaction equation
[OH:1][CH2:2][C:3]1([N:12]2[C:16]3=[C:17]4[S:23][CH:22]=[CH:21][C:18]4=[N:19][CH:20]=[C:15]3[N:14]=[CH:13]2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]#[N:11])[CH2:5][CH2:4]1.O.C(O)(C(F)(F)F)=O.C(#N)C>[Pd].CO>[OH:1][CH2:2][C:3]1([N:12]2[C:16]3=[C:17]4[S:23][CH:22]=[CH:21][C:18]4=[N:19][CH:20]=[C:15]3[N:14]=[CH:13]2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]#[N:11])[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 86717564HCID 86717564, compound

Product 1

HCID 73774917HCID 73774917, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [4-(hydroxymethyl)-4-(1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)cyclohexylidene]acetonitrile (18 mg, 0.055 mmol) and 10% palladium on carbon (5.9 mg) in methanol (0.6 mL) was stirred under an atmosphere of H2 (balloon) for 4.5 h. The mixture was filtered through a pad of Celite and concentrated. The crude residue was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give two isomers. On analytic HPLC (Waters SunFire C18, 2.1×50 mm, 5 μM; flow rate 3 mL/min; Injection volume 2 μL; at gradient from 2 to 80% B in 3 minutes (A=water with 0.025% TFA, B=acetonitrile)): First peak retention time 1.05 min, LCMS calculated for C17H19N4OS (M+H)+: m/z=327.1. Found: 327.0. Second peak retention time 1.13 min, LCMS calculated for C17H19N4OS (M+H)+: m/z=327.1. Found: 327.0.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customThe crude residue was purified
  4. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)
  5. customto give two isomers

Sources & evidence

ORD record
ord-ea7be5d583d04ff2a07cbd1651a119e3
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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