Triethylamine → HCID 131733985, compound

HRID 712089Notes

Reaction equation

HRID 712089 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([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])[CH2:3]1.C(N(CC)CC)C.[CH:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38](Cl)=[O:39])=[CH:32][CH:31]=1>CN(C)C=O>[C:33]1([CH2:36][CH2:37][C:38]([N:2]2[CH2:7][CH2:6][CH2:5][C@H:4]([N:8]3[C:12]4=[C:13]5[S:19][CH:18]=[CH:17][C:14]5=[N:15][CH:16]=[C:11]4[N:10]=[C:9]3[CH:20]([OH:22])[CH3:21])[CH2:3]2)=[O:39])[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 86717543HCID 86717543, compound

Product 1

HCID 131733985HCID 131733985, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (1R)-1-{1-[(3S)-piperidin-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol hydrochloride (15 mg, 0.044 mmol) (Example 50, step 4) and triethylamine (24.7 μL, 0.177 mmol) in N,N-dimethylformamide (0.3 mL) was added benzenepropanoyl chloride (8.6 μL, 0.058 mmol). The resulting mixture was stirred for 90 min at room temperature. The mixture 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 6.5 mg (34%) of the desired product. LCMS calculated for C24H27N4O2S (M+H)+: m/z=435.2. Found: 435.1. 1H NMR (300 MHz, CDCl3) δ 9.07 (s, 1H), 7.71-7.66 (m, 1H), 7.65-7.57 (m, 1H), 7.34-7.27 (m, 2H), 7.26-7.16 (m, 2H), 7.12 (d, J=6.9 Hz, 1H), 5.21 (s, 1H), 4.83 (d, J=13.1 Hz, 2H), 4.78-4.64 (m, 1H), 4.04-3.87 (m, 1H), 3.61-3.23 (m, 3H), 3.04-2.85 (m, 2H), 2.77-2.60 (m, 2H), 2.15 (s, 1H), 1.97 (d, J=14.4 Hz, 1H), 1.81 (d, J=6.5 Hz, 2H), 1.50 (d, J=13.1 Hz, 2H) ppm.

Workup

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

Sources & evidence

ORD record
ord-9df1faceab3340208f29bb27d6972004
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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