HCID 86717556, compound → HCID 73775524, compound

HRID 712103Notes

Reaction equation

HRID 712103 reaction equation
[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]2[C:14]3=[C:15]4[S:21][CH:20]=[CH:19][C:16]4=[N:17][CH:18]=[C:13]3[N:12]=[C:11]2[C@H:22]([OH:24])[CH3:23])[CH2:6][C@H:5]1[NH:25]C(=O)OCC1C=CC=CC=1)#[N:2]>[Pd].CO>[NH2:25][C@@H:5]1[CH2:6][C@@H:7]([N:10]2[C:14]3=[C:15]4[S:21][CH:20]=[CH:19][C:16]4=[N:17][CH:18]=[C:13]3[N:12]=[C:11]2[C@H:22]([OH:24])[CH3:23])[CH2:8][CH2:9][C@@H:4]1[CH2:3][C:1]#[N:2]

Participants

4

Reactant 1

HCID 86717556HCID 86717556, compound

Product 1

HCID 73775524HCID 73775524, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl ((1R,2R,5S)-2-(cyanomethyl)-5-{2-[(1R)-1-hydroxyethyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl}cyclohexyl)carbamate (18 mg, 0.037 mmol) and 10% palladium on carbon (24 mg) in methanol (0.27 mL) was stirred under an atmosphere of H2 (balloon) overnight. The mixture was filtered and concentrated. The crude was purified using prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 3.2 mg of the desired product. LCMS calculated for C18H22N5OS (M+H)+: m/z=356.2. Found: 356.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe crude was purified
  4. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-1abd344f4e1a4667a4cb34bbc14d4f4c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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