Acrylonitrile → HCID 73776049, compound

HRID 711994Notes

Reaction equation

HRID 711994 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3=[C:13]4[S:19][CH:18]=[CH:17][C:14]4=[N:15][CH:16]=[C:11]3[N:10]=[C:9]2[C@H:20]([OH:22])[CH3:21])[CH2:4][CH2:3]1.[C:23](#[N:26])[CH:24]=[CH2:25].N12CCCN=C1CCCCC2>C(#N)C>[OH:22][C@@H:20]([C:9]1[N:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH2:25][CH2:24][C:23]#[N:26])[CH2:3][CH2:4]2)[C:12]2=[C:13]3[S:19][CH:18]=[CH:17][C:14]3=[N:15][CH:16]=[C:11]2[N:10]=1)[CH3:21]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86717455HCID 86717455, compound

Product 1

HCID 73776049HCID 73776049, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1R)-1-(1-piperidin-4-yl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl)ethanol hydrochloride (21.7 mg, 0.0640 mmol) (Example 15, Step 4) in acetonitrile (0.40 mL) was added 2-propenenitrile (8.4 μL, 0.13 mmol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (38 μL, 0.26 mmol). The resulting mixture was stirred at room temperature overnight. After evaporating to dryness, the residue was purified on 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 the desired product (11 mg, 48%). LCMS calculated for C18H22N5OS (M+H)+: m/z=356.2. Found: 356.0.

Workup

  1. customAfter evaporating to dryness
  2. customthe residue was purified on RP-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-63450597c33a4113b6de74403a912f92
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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