Triethylamine → N-{2-[(3-hydroxypiperidin-1-yl)carbonyl]-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl}acetamide

HRID 1715267Notes

Reaction equation

HRID 1715267 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].[OH:19][CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:16]([C:13]2[S:14][CH:15]=[C:11]([C:7]3[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=3[CH3:10])[N:12]=2)=[O:17])[CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 232933-HydroxypiperidineHCID 86621993HCID 86621993, compound

Product 1

HCID 11989752N-{2-[(3-hydroxypiperidin-1-yl)carbonyl]-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl}acetamideYield 42%

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, (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 3-Hydroxypiperidine (Fluka)(67.0 mg; 0.66 mmol; 1 eq.) and triethylamine (0.19 ml; 1.33 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (26) as a brown solid (103 mg; 42%). M− (ESI): 365.20; M+ (ESI): 367.16. HPLC (method A), Rt: 2.35 min (purity: 99.4%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Sources & evidence

ORD record
ord-8e23bf44492d43ef81516ed0e19c4523
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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