Triethylamine → HCID 51354523, compound

HRID 2092965Notes

Reaction equation

HRID 2092965 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:16]1([C:22]#[C:23][C:24]2[S:25][C:26]([C:29](O)=[O:30])=[CH:27][N:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOC(C)=O>[C:16]1([C:22]#[C:23][C:24]2[S:25][C:26]([C:29]([N:2]3[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]3)=[O:30])=[CH:27][N:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30848514-Piperidone hydrochlorideHCID 58227488HCID 58227488, compound3×

Product 1

HCID 51354523HCID 51354523, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Example 75 was prepared via the process of Scheme 1, step 3, Method—B, supra, as follows: 2-Phenylethynyl-thiazole-5-carboxylic acid (0.100 g, 0.436 mmol) in tetrahydrofuran (1.7 mL) [Intermediate 1] was stirred, and N,N′-carbonyldiimidazole (0.079 g, 0.49 mmol) (Fluka Chemie AG) was added in one portion at room temperature. The mixture was stirred for 60 minutes and then 4-piperidone monohydrochloride (0.241 g, 1.78 mmol) (3B Pharmachem (Wuhan) International Co., LTD (Libertyville, Ill., USA)) was added, followed by the addition of triethylamine (192 uL, 1.38 mmol). The mixture was stirred for about 2 hours and was worked up by diluting with 25 mL of EtOAc and washing with 2×10 mL of 1.7% aq. HCl, 1×10 mL of water, 3×10 mL of 1.0 M K2CO3, and 1×10 mL of brine; dried (Na2SO4), and concentrated to give the title compound, 1-(2-phenylethynyl-thiazole-5-carbonyl)-piperidin-4-one (55 mg; 41%), as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.04 (s, 1H), 7.63-7.59 (m, 2H), 7.47-7.32 (m, 3H), 4.03 (t, J=6.3 Hz, 4H), 2.59 (t, J=6.3 Hz, 4H). LC/MS (Method 1), RT=1.05 min. Calculated [M+H]+=311; Observed [M+H]+=311.

Workup

  1. customExample 75 was prepared via the process of Scheme 1, step 3, Method—B, supra
  2. stirringThe mixture was stirred for about 2 hours
  3. washwashing with 2×10 mL of 1.7% aq. HCl, 1×10 mL of water, 3×10 mL of 1.0 M K2CO3, and 1×10 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f730b495f0ce4dc9b08b7b701012e156
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

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