Triethylamine → HCID 11990104, compound

HRID 1715282Notes

Reaction equation

HRID 1715282 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].O.Cl.[NH:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[N:12]=[C:13]([C:16]([N:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)=[O:17])[S:14][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723901PiperonylamineHCID 86621993HCID 86621993, compound

Product 1

HCID 11990104HCID 11990104, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above (160 mg; 0.53 mmol; 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-Piperidone hydrochloride monohydrate (Aldrich) (97.7 mg; 0.64 mmol; 1.20 eq.) and triethylamine (0.22 ml; 1.59 mmol; 3 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is purified by preparative HPLC, affording Compound (42) as a pale yellow powder (39.2 mg; 20%). 1H NMR (DMSO-d6, 300 MHz) δ 2.14 (s, 3H), 2.49 (s, 3H), 2.53 (m, 4H), 3.94 (m, 2H), 4.53 (m, 2H), 8.03 (s, 1H), 12.17 (s, 1H). M− (ESI): 363.09; M+ (ESI): 365.04. HPLC (method A), Rt: 2.44 min (purity: 95.3%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-978dad0c1bb84e669b8444e11fd70186
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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